Sodium borohydride → tert-Butyl 4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

HRID 2168787Notes

Reaction equation

HRID 2168787 reaction equation
C([O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]1)=O)C.[BH4-].[Na+]>CO>[C:16]([O:15][C:13]([N:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH:6]([CH2:4][OH:3])[CH2:7]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 64208761-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate

Product 1

HCID 66717856tert-Butyl 4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (51.59 mmol, 14 g) in methanol (300 mL) was added sodium borohydride (12 g) in 12 portions over 30 min. The reaction mixture was stirred for additional 30 min, and the volatiles were removed under reduced pressure. To the residue was added saturated ammonium chloride (300 mL). The mixture was extracted with ethyl acetate (300 mL), and the organic layer was dried and concentrated under reduced pressure. The residue was purified on a flash silica gel column eluting with ethyl acetate to provide 4-hydroxy-3-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. additionTo the residue was added saturated ammonium chloride (300 mL)
  3. extractionThe mixture was extracted with ethyl acetate (300 mL)
  4. customthe organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on a flash silica gel column
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c3be25c41d0f4120a740315b5de3f708
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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