(S)-tert-Butyl 2-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate → (S)-1-N-Boc-piperidine-2-ethanol

HRID 1857609Notes

Reaction equation

HRID 1857609 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][C@H: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][C@H:15]1[CH2:20][CH2:21][OH:22])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

3

Reactant 2

HCID 10264438(S)-tert-Butyl 2-(2-methoxy-2-oxoethyl)piperidine-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1514243(S)-1-N-Boc-piperidine-2-ethanolYield 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 (S)-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 vigorously 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-10feda1f01b34afcbe926e1e7e71fdd4
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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