No renderable structure data available
CC(C)(C)OC(=O)NCC1(CCCC1)COChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl N-[[1-(hydroxymethyl)cyclopentyl]methyl]carbamate |
|---|---|
| IUPAC Name | — |
| CAS Number | 223763-91-5 |
| Database ID | 57478044 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl N-[[1-(hydroxymethyl)cyclopentyl]methyl]carbamate (CAS 223763-91-5) 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 57478044
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-e94dbe40363f418283e3be42f4d548a4Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e2733171dfaa40228842e1392db45bddConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of oxalyl chloride (456 μL, 5.38 mmol) in DCM (30.0 mL) at −78° C. was added DMSO (637 μL, 8.97 mmol) and the resulting mixture was stirred for 5 minutes. tert-Butyl [1-(hydroxymethyl)cyclopentyl]methylcarbamate (1.03 g, 4.48 mmol) in DCM (10.0 mL) was added and the resulting mixture was stirred for 30 minutes at −78° C. TEA (2.50 mL, 17.9 mmol) was added and the resulting mixture was allowed to warm to ambient temperature over 30 minutes. Water was added. The organic phase was washed sequentially with 0.1 N HCl, water, saturated sodium bicarbonate solution, and brine, and then dried over sodium sulfate and the solvent was removed in vacuo to afford the product (957 mg, 94%). 1H NMR (300 MHz, CDCl3): δ 9.39 (s, 1H), 4.94 (br s, 1H), 3.25 (d, 2H), 1.89-1.46 (m, 8H), 1.41 (s, 9H). the resulting mixture was stirred for 30 minutes at −78° C The organic phase was washed sequentially with 0.1 N HCl, water, saturated sodium bicarbonate solution, and brine dried over sodium sulfate the solvent was removed in vacuo
Source ID: ord-1a149f56c8944f50b6f9c9eaab8e57b3Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of methyl 1-[(tert-butoxycarbonyl)amino]methylcyclopentanecarboxylate (1.50 g, 5.83 mmol) in THF (25.0 mL) at −78° C. was added dropwise 1.0 M diisobutylaluminum hydride in DCM (17.5 mL). The reaction was stirred for 2 hours with slow warming to −10° C. A saturated solution of K/Na tartrate was added, followed by ether. This mixture was stirred for 30 minutes at ambient temperature and the organic layer was separated and washed with water, and brine. The organic layer was then dried over sodium sulfate, and the solvent was removed in vacuo to afford the product (1.03 g, 77%). 1H NMR (300 MHz, CDCl3): 4.90 (br s, 1H), 3.27 (s, 2H), 3.06 (d, 2H), 1.5-1.17 (m, 8H), 1.44 (s, 9H). This mixture was stirred for 30 minutes at ambient temperature the organic layer was separated washed with water, and brine The organic layer was then dried over sodium sulfate the solvent was removed in vacuo
Source ID: ord-b4e6cd393cb1465fb073ff6fc3e34037Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of oxalyl chloride (456 μL, 5.38 mmol) in DCM (30.0 mL) at −78° C. was added DMSO (637 μL, 8.97 mmol) and the resulting mixture was stirred for 5 minutes. tert-Butyl [1-(hydroxymethyl)cyclopentyl]methylcarbamate (1.03 g, 4.48 mmol) in DCM (10.0 mL) was added and the resulting mixture was stirred for 30 minutes at −78° C. TEA (2.50 mL, 17.9 mmol) was added and the resulting mixture was allowed to warm to ambient temperature over 30 minutes. Water was added. The organic phase was washed sequentially with 0.1 N HCl, water, saturated sodium bicarbonate solution, and brine, and then dried over sodium sulfate and the solvent was removed in vacuo to afford the product (957 mg, 94%). 1H NMR (300 MHz, CDCl3): δ□ 9.39 (s, 1H), 4.94 (br s, 1H), 3.25 (d, 2H), 1.89-1.46 (m, 8H), 1.41 (s, 9H). the resulting mixture was stirred for 30 minutes at −78° C The organic phase was washed sequentially with 0.1 N HCl, water, saturated sodium bicarbonate solution, and brine dried over sodium sulfate the solvent was removed in vacuo
Source ID: ord-8d212026231a4663a14138247da8e777Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of methyl 1-[(tert-butoxycarbonyl)amino]methylcyclopentanecarboxylate (1.50 g, 5.83 mmol) in THF (25.0 mL) at −78° C. was added dropwise 1.0 M diisobutylaluminum hydride in DCM (17.5 mL). The reaction was stirred for 2 hours with slow warming to −10° C. A saturated solution of K/Na tartrate was added, followed by ether. This mixture was stirred for 30 minutes at ambient temperature and the organic layer was separated and washed with water, and brine. The organic layer was then dried over sodium sulfate, and the solvent was removed in vacuo to afford the product (1.03 g, 77%). 1H NMR (300 MHz, CDCl3): δ □4.90 (br s, 1H), 3.27 (s, 2H), 3.06 (d, 2H), 1.5-1.17 (m, 8H), 1.44 (s, 9H). This mixture was stirred for 30 minutes at ambient temperature the organic layer was separated washed with water, and brine The organic layer was then dried over sodium sulfate the solvent was removed in vacuo
Source ID: ord-4d12306b14624c5e8cb9c2f0950e1b66Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e94dbe40363f418283e3be42f4d548a4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of oxalyl chloride (456 μL, 5.38 mmol) in DCM (30.0 mL) at −78° C. was added DMSO (637 μL, 8.97 mmol) and the resulting mixture was stirred for 5 minutes. tert-Butyl [1-(hydroxymethyl)cyclopentyl]methylcarbamate (1.03 g, 4.48 mmol) in DCM (10.0 mL) was added and the resulting mixture was stirred for 30 minutes at −78° C. TEA (2.50 mL, 17.9 mmol) was added and the resulting mixture was allowed to warm to ambient temperature over 30 minutes. Water was added. The organic phase was washed sequentially with 0.1 N HCl, water, saturated sodium bicarbonate solution, and brine, and then dried over sodium sulfate and the solvent was removed in vacuo to afford the product (957 mg, 94%). 1H NMR (300 MHz, CDCl3): δ 9.39 (s, 1H), 4.94 (br s, 1H), 3.25 (d, 2H), 1.89-1.46 (m, 8H), 1.41 (s, 9H). the resulting mixture was stirred for 30 minutes at −78° C The organic phase was washed sequentially with 0.1 N HCl, water, saturated sodium bicarbonate solution, and brine dried over sodium sulfate the solvent was removed in vacuo
Source ID: ord-1a149f56c8944f50b6f9c9eaab8e57b3Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of methyl 1-[(tert-butoxycarbonyl)amino]methylcyclopentanecarboxylate (1.50 g, 5.83 mmol) in THF (25.0 mL) at −78° C. was added dropwise 1.0 M diisobutylaluminum hydride in DCM (17.5 mL). The reaction was stirred for 2 hours with slow warming to −10° C. A saturated solution of K/Na tartrate was added, followed by ether. This mixture was stirred for 30 minutes at ambient temperature and the organic layer was separated and washed with water, and brine. The organic layer was then dried over sodium sulfate, and the solvent was removed in vacuo to afford the product (1.03 g, 77%). 1H NMR (300 MHz, CDCl3): 4.90 (br s, 1H), 3.27 (s, 2H), 3.06 (d, 2H), 1.5-1.17 (m, 8H), 1.44 (s, 9H). This mixture was stirred for 30 minutes at ambient temperature the organic layer was separated washed with water, and brine The organic layer was then dried over sodium sulfate the solvent was removed in vacuo
Source ID: ord-b4e6cd393cb1465fb073ff6fc3e34037Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of oxalyl chloride (456 μL, 5.38 mmol) in DCM (30.0 mL) at −78° C. was added DMSO (637 μL, 8.97 mmol) and the resulting mixture was stirred for 5 minutes. tert-Butyl [1-(hydroxymethyl)cyclopentyl]methylcarbamate (1.03 g, 4.48 mmol) in DCM (10.0 mL) was added and the resulting mixture was stirred for 30 minutes at −78° C. TEA (2.50 mL, 17.9 mmol) was added and the resulting mixture was allowed to warm to ambient temperature over 30 minutes. Water was added. The organic phase was washed sequentially with 0.1 N HCl, water, saturated sodium bicarbonate solution, and brine, and then dried over sodium sulfate and the solvent was removed in vacuo to afford the product (957 mg, 94%). 1H NMR (300 MHz, CDCl3): δ□ 9.39 (s, 1H), 4.94 (br s, 1H), 3.25 (d, 2H), 1.89-1.46 (m, 8H), 1.41 (s, 9H). the resulting mixture was stirred for 30 minutes at −78° C The organic phase was washed sequentially with 0.1 N HCl, water, saturated sodium bicarbonate solution, and brine dried over sodium sulfate the solvent was removed in vacuo
Source ID: ord-8d212026231a4663a14138247da8e777Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of methyl 1-[(tert-butoxycarbonyl)amino]methylcyclopentanecarboxylate (1.50 g, 5.83 mmol) in THF (25.0 mL) at −78° C. was added dropwise 1.0 M diisobutylaluminum hydride in DCM (17.5 mL). The reaction was stirred for 2 hours with slow warming to −10° C. A saturated solution of K/Na tartrate was added, followed by ether. This mixture was stirred for 30 minutes at ambient temperature and the organic layer was separated and washed with water, and brine. The organic layer was then dried over sodium sulfate, and the solvent was removed in vacuo to afford the product (1.03 g, 77%). 1H NMR (300 MHz, CDCl3): δ □4.90 (br s, 1H), 3.27 (s, 2H), 3.06 (d, 2H), 1.5-1.17 (m, 8H), 1.44 (s, 9H). This mixture was stirred for 30 minutes at ambient temperature the organic layer was separated washed with water, and brine The organic layer was then dried over sodium sulfate the solvent was removed in vacuo
Source ID: ord-4d12306b14624c5e8cb9c2f0950e1b66Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e2733171dfaa40228842e1392db45bddPubChem References
These sources are listed in the compound's public database record.
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