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

HRID 1948491ノート

反応式

HRID 1948491 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f0b13d3f887247ad8d4bbe1bf98d6ddf
出典データセット
uspto-grants-2013_03
特許番号
US08399451B2

反応ノート

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