Water → 1-Benzyl-4-(hydroxymethyl)piperidin-3-ol

HRID 1351493Notes

Reaction equation

HRID 1351493 reaction equation
[BH4-].[Na+].Cl.[CH2:4]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](OCC)=[O:18])[C:13](=[O:22])[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>CO>[CH2:4]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[CH:13]([OH:22])[CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723880Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 221357071-Benzyl-4-(hydroxymethyl)piperidin-3-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (40 g) was added in portions to a stirred solution of ethyl N-benzyl-3-oxopiperidine-4-carboxylate hydrochloride (23.6 g, 90 mmol) in methanol (500 mL), over 2 h. Water (300 mL) was added slowly, the mixture stirred for 15 min and then the organics were evaporated. The residue was partitioned between DCM and water (×3), the combined organic layers dried over anhydrous sodium sulfate, and the solvent evaporated to give 1-benzyl-4-hydroxymethyl-piperidin-3-ol product as a cis/trans mixture, which was used in the next step without further purification. M.S (M+1): 222.

Workup

  1. customthe organics were evaporated
  2. customThe residue was partitioned between DCM and water (×3)
  3. dry with materialthe combined organic layers dried over anhydrous sodium sulfate
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-954131ddf88f498990c01ac1d6b78e0e
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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