Water → HCID 56771127, compound

HRID 632727Notes

Reaction equation

HRID 632727 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+].[OH2:18]>CO.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:18])[CH2:9][N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21802639HCID 21802639, compound

Product 1

HCID 56771127HCID 56771127, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(3-fluoro-phenyl)-2-piperidin-1-yl-ethan Intermediate (64.1) (1.50 g; 6.78 mmol; 1.00 eq.) in MeOH (15 mL) was added sodium borohydride (0.38 g; 10.17 mmol; 1.50 eq.) and 1 mL of water and 1 drop of 10% NaOH. Then the mixture was stirred at 50° C. for 5 hours. The reaction mixture was partitioned between CHCl3 and water. The organic layer was separated, dried over MgSO4 and concentrated. The residue was purified through flash chromatography on silica gel to yield 1-(3-fluoro-phenyl)-2-piperidin-1-yl-ethanol. LC-MS: 224 (M+H).

Workup

  1. customThe reaction mixture was partitioned between CHCl3 and water
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified through flash chromatography on silica gel

Sources & evidence

ORD record
ord-517050105f154146a02a4654a2a4e45a
Source dataset
uspto-grants-2016_04
Patent number
US09321760B2

Reaction notes

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