Sodium borohydride → 8-[(4-Bromophenyl)methyl]-8-azabicyclo[3.2.1]octan-3-ol

HRID 1888481Notes

Reaction equation

HRID 1888481 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][N:9]2[CH:14]3[CH2:15][CH2:16][CH:10]2[CH2:11][C:12](=[O:17])[CH2:13]3)=[CH:6][CH:5]=1>CO.O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH:14]3[CH2:15][CH2:16][CH:10]2[CH2:11][CH:12]([OH:17])[CH2:13]3)=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 551064698-(4-Bromobenzyl)-8-aza-bicyclo[3.2.1]octan-3-one

Product 1

HCID 582668338-[(4-Bromophenyl)methyl]-8-azabicyclo[3.2.1]octan-3-olYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (95 mg, 1.50 mmol) was added to a solution of 8-(4-bromobenzyl)-8-azabicyclo-[3.2.1]octan-3-one (0.22 g, 0.75 mmol) in methanol (10 mL) and the reaction mixture was stirred for 30 minutes. The reaction was diluted with water (10 mL) and extracted into DCM (3×20 mL). The combined organic layer was washed with saturated aqueous sodium bicarbonate solution (10 mL), dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as an off-white solid (200 mg, 90%). 1H NMR (CDCl3, 300 MHz): 7.43 (dd, J=8.3, 2.0 Hz, 3H), 7.29-7.23 (m, 2H), 3.60-3.45 (m, 2H), 3.23-3.10 (m, 2H), 2.16-1.40 (m, 8H). LCMS (Method B): RT=1.90 min, M+H+=296/298.

Workup

  1. extractionextracted into DCM (3×20 mL)
  2. washThe combined organic layer was washed with saturated aqueous sodium bicarbonate solution (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-6adca4a476cc4e1ebc5b4e81b1b03cdc
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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