Sodium borohydride → 1-Tert-butyl 3-methyl 4-hydroxypiperidine-1,3-dicarboxylate

HRID 2115674Notes

Reaction equation

HRID 2115674 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[C:15]([O:17][CH3:18])=[O:16].[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][CH:3]1[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 112768931-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate

Product 1

HCID 185348061-Tert-butyl 3-methyl 4-hydroxypiperidine-1,3-dicarboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold (0° C.) solution of 1-tert-butyl 3-methyl 4-oxo-1,3-piperidinedicarboxylate (134.0 g, 520.8 mmol) in methanol (800 mL) was added NaBH4 (9.85 g, 260.4 mmol) portionwise. The resulting mixture was stirred overnight to be allowed to warm to room temperature. The solvent was removed under reduced pressure, the residue was dissolved into ethyl acetate, washed with brine, dried over MgSO4, filterd, and concentrated under reduced pressure to give 1-tert-butyl 3-methyl 4-hydroxy-1,3-piperidinedicarboxylate, which was used for the next reaction without further purification. (120.8 g, yield 90%)

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved into ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over MgSO4, filterd
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8bda5a9c62c14c4db63c59660261a931
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

Loading…