Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → HCID 59201466、化合物

HRID 451715

反応式

HRID 451715 の反応式
[Si]([O:8][CH2:9][CH2:10][O:11][C@:12]([C@@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]1)([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1)[CH3:13])(C(C)(C)C)(C)C.[F-].C([N+](CC)(CC)CC)C>CC#N>[Cl:20][C:16]1[CH:15]=[C:14]([C@@:12]([C@@H:21]2[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]2)([O:11][CH2:10][CH2:9][OH:8])[CH3:13])[CH:19]=[CH:18][CH:17]=1

参加物

4

反応物 2

HCID 69582Ethanaminium, N,N,N-triethyl-, fluoride (1:1)HCID 59201381HCID 59201381、化合物

生成物 1

HCID 59201466HCID 59201466、化合物収率 35%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
45 °C

実験手順

A mixture of (R)-tert-butyl 3-((R)-1-(2-(tert-butyldimethylsilyloxy)ethoxy)-1-(3-chlorophenyl)ethyl)piperidine-1-carboxylate, tetraethylammonium fluoride (7.600 g, 50.9 mmol) in CH3CN was heated at 45° C. for 1 h and then was allowed to stir at rt overnight. The reaction mixture was evaporated under reduced pressure, the residue was dissolved into water and extracted with Et2O (3×), dried over Na2SO4. After the solvent was removed in vacuo, the crude product was purified by reversed-phase HPLC to give 1.000 g (35% in two steps) of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-hydroxyethoxy)ethyl)piperidine-1-carboxylate. MS ESI +ve m/z 406 (M+Na).

後処理

  1. customThe reaction mixture was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved into water
  3. extractionextracted with Et2O (3×)
  4. dry with materialdried over Na2SO4
  5. customAfter the solvent was removed in vacuo
  6. customthe crude product was purified by reversed-phase HPLC

出典と根拠

ORDレコード
ord-848e0f9c20c841f79ce5223618f2da14
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

関連ノート

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