Borane → Tert-butyl 4-hydroxy-4-(2-hydroxyethyl)piperidine-1-carboxylate

HRID 403512Notes

Reaction equation

HRID 403512 reaction equation
B.C1COCC1.[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]([CH2:21][C:22](O)=[O:23])([OH:20])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>>[C:7]([O:11][C:12]([N:14]1[CH2:15][CH2:16][C:17]([OH:20])([CH2:21][CH2:22][OH:23])[CH2:18][CH2:19]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 3

HCID 6331BoraneHCID 8028TetrahydrofuranHCID 100611062-{1-[(Tert-butoxy)carbonyl]-4-hydroxypiperidin-4-yl}acetic acid

Product 1

HCID 21936021Tert-butyl 4-hydroxy-4-(2-hydroxyethyl)piperidine-1-carboxylate

Conditions

Temperature
0 °C

Procedure

1M solution of borane in THF (15.8 ml, 15.8 mmol) was added slowly to a solution of 2-(1-(tert-butoxycarbonyl)-4-hydroxypiperidin-4-yl)acetic acid (40) (1.02 g, 3.94 mmol) at 0° C. After stirring the mixture at 0° C. for 1 hour and at rt for 16 hours the reaction was quenched by addition of NH4Cl solution and extracted with ethyl acetate. The organic layer was then washed with water and brine, dried over Na2 SO4 and evaporated. The crude product was purified by flash chromatography (silica gel, EtOAc/n-pentane) which furnished the product as colorless oil.

Workup

  1. customat rt for 16 hours the reaction was quenched by addition of NH4Cl solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was then washed with water and brine
  4. customdried over Na2 SO4
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (silica gel, EtOAc/n-pentane) which

Sources & evidence

ORD record
ord-b208fdf1ebec4170a6cb918357e4430c
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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