Sodium borohydride → tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

HRID 1873829Notes

Reaction equation

HRID 1873829 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:8][CH2:9]1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 109879834-Acetyl-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 21989903tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 4-acetylpiperidine-1-carboxylate from the previous step was dissolved in 50 ml methanol. NaBH4 (2.01 g, 53 mmol) was added in batches at 0° C. The resulting reaction mixture was stirred at 0° C. for 30 minutes. The volatiles were removed under vacuum. The residue was partitioned between 150 ml 10% KOH solution and 200 ml ether. The organic layers were washed with 100 ml brine, dried over sodium sulfate and concentrated to give 22.5 g colorless oil, which was azotropically dried by addition of 50 ml toluene and reconcentration under vacuum. This material was used for next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. customThe volatiles were removed under vacuum
  3. customThe residue was partitioned between 150 ml 10% KOH solution and 200 ml ether
  4. washThe organic layers were washed with 100 ml brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-544e16aaf4984e5694219b29d01041c5
Source dataset
uspto-grants-2012_11
Patent number
US08304434B2

Reaction notes

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