Sodium borohydride → Tert-butyl 4-hydroxy-2-methylpiperidine-1-carboxylate

HRID 386534Notes

Reaction equation

HRID 386534 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+]>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

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12992764tert-Butyl 2-methyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 22181172Tert-butyl 4-hydroxy-2-methylpiperidine-1-carboxylateYield 101.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 2-methyl-4-oxopiperidine-1-carboxylate (727 mg, 3.41 mmol, Small Molecules Inc.) in MeOH (6.0 mL) at 0° C. was added sodium borohydride (193 mg, 5.11 mmol, Aldrich) in several portions. The reaction mixture was stirred at 0° C. for 1 hr and warmed up to room temperature and continuously stirred for another 2.5 hrs. The resulting mixture was then quenched with saturated NH4Cl aqueous solution and evaporated under reduced pressure to remove MeOH followed by extraction with CH2Cl2 (3×). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound (745 mg) as a colorless sticky oil which was used without further purification.

Workup

  1. temperaturewarmed up to room temperature
  2. stirringcontinuously stirred for another 2.5 hrs
  3. customThe resulting mixture was then quenched with saturated NH4Cl aqueous solution
  4. customevaporated under reduced pressure
  5. customto remove MeOH
  6. extractionfollowed by extraction with CH2Cl2 (3×)
  7. dry with materialThe combined extracts were dried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b1d7a841b854dd2856015d2459a8921
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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