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

HRID 1948491노트

반응식

HRID 1948491 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f0b13d3f887247ad8d4bbe1bf98d6ddf
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399451B2

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