Methyl N-boc-2-piperidineacetate → Tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate

HRID 1275596Notes

Reaction equation

HRID 1275596 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[CH2:20][C:21](OC)=[O:22])=[O:13])([CH3:10])([CH3:9])[CH3:8]>>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[CH2:20][CH2:21][OH:22])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

3

Reactant 2

HCID 11572435Methyl N-boc-2-piperidineacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 5103438Tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylateYield 94.6%

Procedure

To a slurry of lithium aluminum hydride (580 mg in 65 mL dry diethyl ether) at 0° C. was added dropwise a solution of 2-(methoxycarbonylmethyl)piperidine-1-carboxylic acid tert-butyl ester (5.47 g in 40 mL dry diethyl ether) over a period of 30 minutes. The reaction was allowed to continue at 0° C. for an additional hour, at which time it was quenched by the careful addition of 0.58 mL water followed by 0.58 mL 2N sodium hydroxide and 1.8 mL water. The resulting suspension was stirred vigourously for 30 minutes then filtered through diatomaceous earth. The filtrate was concentrated in vacuo and the residue purified by flash chromatography on silica gel (hexane:ethyl acetate, 6:4) to give the title compound (4.61 g).

Workup

  1. waitto continue at 0° C. for an additional hour, at which time it
  2. customwas quenched by the careful addition of 0.58 mL water
  3. filtrationthen filtered through diatomaceous earth
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue purified by flash chromatography on silica gel (hexane:ethyl acetate, 6:4)

Sources & evidence

ORD record
ord-c99ab651b0334605b5a618152f452e06
Source dataset
uspto-grants-2000_12
Patent number
US06162813

Reaction notes

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