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

HRID 412247Notes

Reaction equation

HRID 412247 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-afe1f4cc8885463988cfec851b8ebf4e
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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