6-bromo-2,3-dihydro-1H-inden-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Bromoindan-1-ol (3.01 g) and dihydropyrane (1.78 g) are dissolved in dichloromethane (50 ml), and thereto is added pyridinium p-toluenesulfonate (178 mg), and the mixture is stirred at room temperature for 1.5 hour. The reaction solution is washed with a saturated aqueous sodium hydrogen carbonate solution, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate) to give 6-bromo-1-tetrahydropyranyloxyindane (4.10 g). The reaction solution is washed with a saturated aqueous sodium hydrogen carbonate solution dried evaporated to remove the solvent The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 6-Bromo-2,3-dihydro-1H-inden-1-ol (300 mg, 1.41 mmol) in CH2Cl2 (4 mL) was added 2,6-lutidine (151 μL, 1.41 mmol) followed by triisopropylsilyltriflate (378 μL, 1.41 mmol) at room temperature. The reaction was stirred for 30 min then added to 1N HCl and extracted. The organic layer was washed with saturated sodium bicarbonate then brine and dried over MgSO4. The solvent was removed in vacuo and the crude material purified by column chromatography. extracted The organic layer was washed with saturated sodium bicarbonate brine and dried over MgSO4 The solvent was removed in vacuo the crude material purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 6-Bromo-2,3-dihydro-1H-inden-1-ol (300 mg, 1.41 mmol) in CH2Cl2 (4 mL) was added 2,6-lutidine (151 μL, 1.41 mmol) followed by triisopropylsilyltriflate (378 μL, 1.41 mmol) at room temperature. The reaction was stirred for 30 min then added to 1N HCl and extracted. The organic layer was washed with saturated sodium bicarbonate then brine and dried over MgSO4. The solvent was removed in vacuo and the crude material purified by column chromatography. extracted The organic layer was washed with saturated sodium bicarbonate brine and dried over MgSO4 The solvent was removed in vacuo the crude material purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-bromoindanol (0.51 g, 2.4 mmol) in anhydrous tetrahydrofuran (10 mL), was added sodium hydride (0.097 g, 3.84 mmol) over a period of five minutes at room temperature. The reaction mixture was stirred at room temperature for fifteen minutes and iodomethane (0.22 mL, 3.6 mmol) was added. After thirty minutes at room temperature, the reaction mixture was partitioned between ethyl acetate (20 mL) and water (20 mL). The ethyl acetate layer was washed with brine (20 mL), dried over sodium sulfate and concentrated to yield the title compound (0.485 g, 89%). 1H NMR (CDCl3) : □ 7.5 (s, 1H), 7.3 (d, 1H), 7.0 (d, 1H), 4.7 (m, 1H), 3.3 (s, 3H), 3.0 (m, 1H), 2.7 (m, 1H), 2.3 (m, 1H), 2.0 (m, 1H). After thirty minutes at room temperature the reaction mixture was partitioned between ethyl acetate (20 mL) and water (20 mL) The ethyl acetate layer was washed with brine (20 mL) dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-bromoindanol (0.3 g, 1.39 mmol) was subjected to the same conditions as 104, part A by substituting methylamine with pyrrolidine (1.16 mL, 14 mmol) to yield the title compound (0.195 g, 52%). 1H NMR (CDCl3): 7.4 (s, 1H), 7.25 (d, 1H), 7.0 (d, 1H), 4.1 (t, 1H), 2.9 (m, 1H), 2.6 (m, 1H), 2.55 (m, 4H), 2.1 (m, 2H), 1.7 (brs, 4H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-bromoindanol (0.3 g, 1.39 mmol) was subjected to the same conditions as 104, part A by substituting methylamine with pyrrolidine (1.16 mL, 14 mmol) to yield the title compound (0.195 g, 52%). 1H NMR (CDCl3): 7.4 (s, 1H), 7.25 (d, 1H), 7.0 (d, 1H), 4.1 (t, 1H), 2.9 (m, 1H), 2.6 (m, 1H), 2.55 (m, 4H), 2.1 (m, 2H), 1.7 (brs, 4H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-bromo-1-indanone (prepared as described by Cornelius, Lyndon A. M. and Combs, Donald W. Synth. Commun. (1994), 24(19), 2777-88) (1.4 g, 6.57 mmol) in 20 mL of methanol was added sodium borohydride (0.087 g, 2.3 mmol) over a period of five minutes at room temperature. The reaction mixture was stirred for two hours at room temperature, concentrated under pressure and partitioned between ethyl acetate (50 mL) and 1N HCl (20 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure to yield the title compound as a solid (1.4 g, 99%). 1H NMR (CDCl3): δ 7.45 (s, 1H), 7.3 (d, 1H), 7.0 (d, 1H), 5.2 (t, 1H), 2.9 (m, 1H), 2.7 (m, 1H), 2.4 (m, 1H), 1.9 (m, 2H). concentrated under pressure partitioned between ethyl acetate (50 mL) and 1N HCl (20 mL) The ethyl acetate layer was dried over sodium sulfate concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Bromoindan-1-ol (3.01 g) and dihydropyrane (1.78 g) are dissolved in dichloromethane (50 ml), and thereto is added pyridinium p-toluenesulfonate (178 mg), and the mixture is stirred at room temperature for 1.5 hour. The reaction solution is washed with a saturated aqueous sodium hydrogen carbonate solution, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate) to give 6-bromo-1-tetrahydropyranyloxyindane (4.10 g). The reaction solution is washed with a saturated aqueous sodium hydrogen carbonate solution dried evaporated to remove the solvent The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir: