No renderable structure data available
OCCC(C)N1CCCC1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-(1-PYRROLIDINYL)-1-BUTANOL |
|---|---|
| IUPAC Name | — |
| CAS Number | 158261-95-1 |
| Database ID | 10012019 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-(1-PYRROLIDINYL)-1-BUTANOL (CAS 158261-95-1) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 10012019
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-96f2a400f1e441a79b4da982e1188716Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Pyrrolidin-1-yl-butan-1-ol (1.0 g, 7 mmol) was dissolved in DCM (20 ml). The reaction was cooled to 0-5° C. and thionyl chloride (1.65 g, 14 mmol) was added slowly. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was concentrated in vacuo and azeotroped with DCM (20 ml) to give the title compound (1.4 g, 100%) as a brown oil. to warm to room temperature The reaction was concentrated in vacuo azeotroped with DCM (20 ml)
Source ID: ord-d8b7f112d61f4bafbed1a8cb727954e9Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Pyrrolidin-1-yl-butan-1-ol (1.0 g, 7 mmol) was dissolved in DCM (20 ml). The reaction was cooled to 0-5° C. and thionyl chloride (1.65 g, 14 mmol) was added slowly. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was concentrated in vacuo and azeotroped with DCM (20 ml) to give the title compound (1.4 g, 100%) as a brown oil. to warm to room temperature The reaction was concentrated in vacuo azeotroped with DCM (20 ml)
Source ID: ord-d8b7f112d61f4bafbed1a8cb727954e9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (925 mg, 3.93 mmol), 3-pyrrolidin-1-yl-butan-1-ol (450 mg, 3.14 mmol), PPh3 (1.03 g, 3.93 mmol), THF (9 ml) and DIAD (0.77 ml, 3.93 mmol) were reacted together according to general procedure C. The crude material was subjected to chromatography on silica eluting with DCM:MeOH (99.5:0.5) to provide the title compound (268 mg, 24%) as a colourless oil. 1H NMR (400 MHz, CDCl3) δ7.21 (d, 2H), 6.88 (d, 2H), 4.11-3.97 (m, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 2.66-2.52 (m, 5H), 2.40 (s, 2H), 2.19-2.05 (m, 3H), 1.96 (s, 6H), 1.93-1.70 (m, 7H), 1.16 (d, 3H).
Source ID: ord-2815ef7c8a574562bb29e07f663c0992Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (925 mg, 3.93 mmol), 3-pyrrolidin-1-yl-butan-1-ol (450 mg, 3.14 mmol), PPh3 (1.03 g, 3.93 mmol), THF (9 ml) and DIAD (0.77 ml, 3.93 mmol) were reacted together according to general procedure C. The crude material was subjected to chromatography on silica eluting with DCM:MeOH (99.5:0.5) to provide the title compound (268 mg, 24%) as a colourless oil. 1H NMR (400 MHz, CDCl3) δ7.21 (d, 2H), 6.88 (d, 2H), 4.11-3.97 (m, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 2.66-2.52 (m, 5H), 2.40 (s, 2H), 2.19-2.05 (m, 3H), 1.96 (s, 6H), 1.93-1.70 (m, 7H), 1.16 (d, 3H).
Source ID: ord-2815ef7c8a574562bb29e07f663c0992Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Pyrrolidine (28.159, 0.4 mol), toluene (200 ml), catalytic p-TsOH (200 mg) and ethyl acetoacetate (20 g, 0.15 mol) were refluxed together in a Dean-Stark apparatus under N2 for 3 hours. The reaction was cooled to room temperature and concentrated in vacuo. NaBH4 (3.1 g, 82 mmol) was dissolved in MeOH (50 ml) and cooled to 0-5° C. A portion of the previous crude reaction (5 g, 27 mmol) in MeOH (25 ml) was added to the reaction mixture and stirred for 72 hours. The reaction was quenched with an aqueous solution of NaOH (1% w/w, 50 ml) and concentrated in vacuo. The aqueous phase was extracted with TBME (3×50 ml). The combined organic extracts were dried over MgSO4, filtered, washed with TBME and concentrated in vacuo to give a mixture of the title compound, 3-pyrrolidin-1-yl-butanoic acid ethyl ester and residual TBME (3.5 g). The mixture (3.5 g) in THF (20 ml) was added to a solution of LiALH4 (1M in THF, 33.5 ml, 33.5 mmol) at 0-5° C. under N2. The reaction was allowed to warm to room temperature and stirred for 3 hours. The reaction was quenched with an aqueous solution of NaOH (1% w/w, 50 ml) at 0-5° C., filtered and washed with THF (3×20 ml). The combined organic layers were dried over MgSO4, filtered, washed with THF and concentrated in vacuo to give the title compound as a yellow oil (2 g, 73%). concentrated in vacuo cooled to 0-5° C was added to the reaction mixture The reaction was quenched with an aqueous solution of NaOH (1% w/w, 50 ml) concentrated in vacuo The aqueous phase was extracted with TBME (3×50 ml) The combined organic extracts were dried over MgSO4 filtered washed with TBME concentrated in vacuo to give
Source ID: ord-652a2f8d29424460b4da5603e29a79f9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Pyrrolidine (28.159, 0.4 mol), toluene (200 ml), catalytic p-TsOH (200 mg) and ethyl acetoacetate (20 g, 0.15 mol) were refluxed together in a Dean-Stark apparatus under N2 for 3 hours. The reaction was cooled to room temperature and concentrated in vacuo. NaBH4 (3.1 g, 82 mmol) was dissolved in MeOH (50 ml) and cooled to 0-5° C. A portion of the previous crude reaction (5 g, 27 mmol) in MeOH (25 ml) was added to the reaction mixture and stirred for 72 hours. The reaction was quenched with an aqueous solution of NaOH (1% w/w, 50 ml) and concentrated in vacuo. The aqueous phase was extracted with TBME (3×50 ml). The combined organic extracts were dried over MgSO4, filtered, washed with TBME and concentrated in vacuo to give a mixture of the title compound, 3-pyrrolidin-1-yl-butanoic acid ethyl ester and residual TBME (3.5 g). The mixture (3.5 g) in THF (20 ml) was added to a solution of LiALH4 (1M in THF, 33.5 ml, 33.5 mmol) at 0-5° C. under N2. The reaction was allowed to warm to room temperature and stirred for 3 hours. The reaction was quenched with an aqueous solution of NaOH (1% w/w, 50 ml) at 0-5° C., filtered and washed with THF (3×20 ml). The combined organic layers were dried over MgSO4, filtered, washed with THF and concentrated in vacuo to give the title compound as a yellow oil (2 g, 73%). concentrated in vacuo cooled to 0-5° C was added to the reaction mixture The reaction was quenched with an aqueous solution of NaOH (1% w/w, 50 ml) concentrated in vacuo The aqueous phase was extracted with TBME (3×50 ml) The combined organic extracts were dried over MgSO4 filtered washed with TBME concentrated in vacuo to give
Source ID: ord-652a2f8d29424460b4da5603e29a79f9Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Pyrrolidin-1-yl-butan-1-ol (1.0 g, 7 mmol) was dissolved in DCM (20 ml). The reaction was cooled to 0-5° C. and thionyl chloride (1.65 g, 14 mmol) was added slowly. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was concentrated in vacuo and azeotroped with DCM (20 ml) to give the title compound (1.4 g, 100%) as a brown oil. to warm to room temperature The reaction was concentrated in vacuo azeotroped with DCM (20 ml)
Source ID: ord-d8b7f112d61f4bafbed1a8cb727954e9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (925 mg, 3.93 mmol), 3-pyrrolidin-1-yl-butan-1-ol (450 mg, 3.14 mmol), PPh3 (1.03 g, 3.93 mmol), THF (9 ml) and DIAD (0.77 ml, 3.93 mmol) were reacted together according to general procedure C. The crude material was subjected to chromatography on silica eluting with DCM:MeOH (99.5:0.5) to provide the title compound (268 mg, 24%) as a colourless oil. 1H NMR (400 MHz, CDCl3) δ7.21 (d, 2H), 6.88 (d, 2H), 4.11-3.97 (m, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 2.66-2.52 (m, 5H), 2.40 (s, 2H), 2.19-2.05 (m, 3H), 1.96 (s, 6H), 1.93-1.70 (m, 7H), 1.16 (d, 3H).
Source ID: ord-2815ef7c8a574562bb29e07f663c0992Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Pyrrolidine (28.159, 0.4 mol), toluene (200 ml), catalytic p-TsOH (200 mg) and ethyl acetoacetate (20 g, 0.15 mol) were refluxed together in a Dean-Stark apparatus under N2 for 3 hours. The reaction was cooled to room temperature and concentrated in vacuo. NaBH4 (3.1 g, 82 mmol) was dissolved in MeOH (50 ml) and cooled to 0-5° C. A portion of the previous crude reaction (5 g, 27 mmol) in MeOH (25 ml) was added to the reaction mixture and stirred for 72 hours. The reaction was quenched with an aqueous solution of NaOH (1% w/w, 50 ml) and concentrated in vacuo. The aqueous phase was extracted with TBME (3×50 ml). The combined organic extracts were dried over MgSO4, filtered, washed with TBME and concentrated in vacuo to give a mixture of the title compound, 3-pyrrolidin-1-yl-butanoic acid ethyl ester and residual TBME (3.5 g). The mixture (3.5 g) in THF (20 ml) was added to a solution of LiALH4 (1M in THF, 33.5 ml, 33.5 mmol) at 0-5° C. under N2. The reaction was allowed to warm to room temperature and stirred for 3 hours. The reaction was quenched with an aqueous solution of NaOH (1% w/w, 50 ml) at 0-5° C., filtered and washed with THF (3×20 ml). The combined organic layers were dried over MgSO4, filtered, washed with THF and concentrated in vacuo to give the title compound as a yellow oil (2 g, 73%). concentrated in vacuo cooled to 0-5° C was added to the reaction mixture The reaction was quenched with an aqueous solution of NaOH (1% w/w, 50 ml) concentrated in vacuo The aqueous phase was extracted with TBME (3×50 ml) The combined organic extracts were dried over MgSO4 filtered washed with TBME concentrated in vacuo to give
Source ID: ord-652a2f8d29424460b4da5603e29a79f9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The target compound was obtained by the method according to Example 18, using 3-pyrrolidin-1-yl-butan -1-ol (racemic mixture) manufactured by the method described in the literature (J. Org. Chem., 1949, Vol. 14, p. 862) and 4-nitrofluorobenzene as starting materials. The target compound was obtained by the method
Source ID: ord-8e4e44cd89b64c8a9359a241434c1d9aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The target compound was obtained by the method according to Example 18, using 3-pyrrolidin-1-yl-butan-1-ol (racemic mixture) manufactured by the method described in the literature (J. Org. Chem., 1949, Vol. 14, p. 862) and 4-nitrofluorobenzene as starting materials. The target compound was obtained by the method
Source ID: ord-1f9d19c1c5d849379500430c4db97b9fPubChem References
These sources are listed in the compound's public database record.
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