Water → Tert-butyl 4-hydroxy-2-methylpiperidine-1-carboxylate

HRID 1928627Notes

Reaction equation

HRID 1928627 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[CH2:5][CH2:4][N:3]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[BH4-].[Na+].O.C(OCC)(=O)C>CO>[OH:8][CH:6]1[CH2:5][CH2:4][N:3]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:2]([CH3:1])[CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 12992764tert-Butyl 2-methyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 22181172Tert-butyl 4-hydroxy-2-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 2-methyl-4-oxopiperidine-1-carboxylate (0.94 g, 4.41 mmol) in methanol (5 mL) was added sodium borohydride (0.22 g, 5.73 mmol) and the reaction was stirred at room temperature for 1 h. Water was added slowly, followed by ethyl acetate. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo to afford the desired product as a mixture of four stereoisomers, which was used in the next step without further purification.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-008758167fd245428db857bad9bf53c8
Source dataset
uspto-grants-2012_05
Patent number
US08183381B2

Reaction notes

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