Sodium borohydride → ethyl 2-((3R)-1-(2-(4-cyanophenyl)-2-hydroxyethyl)piperidin-3-yl)acetate

HRID 1948491Notes

Reaction equation

HRID 1948491 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:23])[CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12]2)=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([OH:23])[CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12]2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58374115(R)-ethyl 2-(1-(2-(4-cyanophenyl)-2-oxoethyl)piperidin-3-yl)acetate

Product 1

HCID 66955736ethyl 2-((3R)-1-(2-(4-cyanophenyl)-2-hydroxyethyl)piperidin-3-yl)acetateYield 57.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of (R)-ethyl 2-(1-(2-(4-cyanophenyl)-2-oxoethyl)piperidin-3-yl)acetate (1 g, 3.18 mmol) in MeOH was added sodium borohydride (0.120 g, 3.18 mmol). The reaction mixture was stirred for 1 hour. The reaction was quenched with water. The reaction mixture was diluted with ethyl acetate and washed with H2O. The organic layer was dried with MgSO4, filtered, and concentrated. The resulting solids were purified on a silica gel cartridge using an EtOAc/hexanes gradient to give 575 mg of ethyl 2-((3R)-1-(2-(4-cyanophenyl)-2-hydroxyethyl)piperidin-3-yl)acetate.

Workup

  1. customThe reaction was quenched with water
  2. additionThe reaction mixture was diluted with ethyl acetate
  3. washwashed with H2O
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solids were purified on a silica gel cartridge

Sources & evidence

ORD record
ord-f0b13d3f887247ad8d4bbe1bf98d6ddf
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

Loading…