Ammonium Chloride → tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

HRID 1846618Notes

Reaction equation

HRID 1846618 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:16])[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:16])[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 109879834-Acetyl-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 21989903tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylateYield 96.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.400 g (1.76 mmol) of 4-acetyl-piperidine-1-carboxylic acid tert-butyl ester in ethanol (3 mL) is added 0.134 g (3.52 mmol) of sodium borohydride. The mixture is stirred at room temperature for 1 hour then a saturated aqueous solution of ammonium chloride is added to consume excess reactants. The mixture is washed with ethyl acetate and the combined organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide 0.390 g (96.6%) of 4-(1-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil.

Workup

  1. customto consume excess reactants
  2. washThe mixture is washed with ethyl acetate
  3. dry with materialthe combined organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a8f3e6c1c76f4cb0b106e7c11f4099d4
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

Loading…