Sodium hydride → (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2,2-dimethoxypropoxy)methyl)piperidine-1-carboxylate

HRID 451916ノート

反応式

HRID 451916 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:22])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:26][C:27]([O:31][CH3:32])([O:29][CH3:30])[CH3:28]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([O:22][CH2:26][C:27]([O:31][CH3:32])([O:29][CH3:30])[CH3:28])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:10]2)[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 671751-Bromo-2,2-dimethoxypropaneHCID 44555022tert-Butyl (R)-3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate

生成物 1

HCID 59201517(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2,2-dimethoxypropoxy)methyl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A mixture of (R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate (0.2234 g, 0.68 mmol), 60% NaH (1.460 g, 36.5 mmol), and 1-bromo-2,2-dimethoxypropane (7.760 g, 42.4 mmol) in THF (20 mL) was heated at 80° C. for 3 d and then cooled to rt. The reaction mixture was then quenched with water, extracted with ethyl acetate (3×), and dried over Na2SO4. After the solvent was evaporated under reduced pressure, the crude product (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2,2-dimethoxypropoxy)methyl)piperidine-1-carboxylate was directly used in the next step without further purification.

後処理

  1. temperaturecooled to rt
  2. customThe reaction mixture was then quenched with water
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialdried over Na2SO4
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe crude product (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2,2-dimethoxypropoxy)methyl)piperidine-1-carboxylate was directly used in the next step without further purification

出典と根拠

ORDレコード
ord-b745b5923a5b42bcaae61184481f9155
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

反応ノート

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