(+/-)-(2R,3R)-1-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-[(3-chloro-4-cyano-2-methylphenylamino)-methyl]piperidine → (+/-)-(2S,3R)-3-(tert-Butyldimethylsilanyloxy)-2-[(3-chloro-4-cyano-2-methylphenylamino)methyl]piperidine

HRID 501648ノート

反応式

HRID 501648 の反応式
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C@H:9]1[CH2:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([Cl:32])[C:25]=1[CH3:33])=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Si:15]([O:14][C@@H:10]1[CH2:11][CH2:12][CH2:13][NH:8][C@H:9]1[CH2:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([Cl:32])[C:25]=1[CH3:33])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17]

参加物

3

反応物 1

HCID 59754257(+/-)-(2R,3R)-1-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-[(3-chloro-4-cyano-2-methylphenylamino)-methyl]piperidine

生成物 1

HCID 68459464(+/-)-(2S,3R)-3-(tert-Butyldimethylsilanyloxy)-2-[(3-chloro-4-cyano-2-methylphenylamino)methyl]piperidine収率 89%

試薬・触媒・溶媒 1

HCID 21863450Trifluoroacetic acid methylene chloride溶媒

実験手順

A solution of 77G (170 mg, 0.34 mmol) in 5% TFA/DCM (5 mL) was stirred at rt for 5 h and LC-MS showed completion. The mixture was concentrated and the residue was dissolved in EtOAc (30 mL), washed with saturated sodium bicarbonate solution (15 mL), brine (10 mL), dried (MgSO4) and evaporated to give desired product 77H (121 m, 89%) as a white solid: Rf (10% MeOH/DCM) 0.39; HPLC (Phenomenex Luna 5 u C18 4.6×50 mm, linear gradient over 4 min) retention time 3.2 min (100%); MS (ES) m/z 344.1 [M+H]+; HRMS calcd for C20H33N3OSiCl 394.2081, Found 394.2080.

後処理

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in EtOAc (30 mL)
  3. washwashed with saturated sodium bicarbonate solution (15 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated

出典と根拠

ORDレコード
ord-e5ddd73460b9495f9bdc89dcafff848d
出典データセット
uspto-grants-2010_08
特許番号
US07772267B2

反応ノート

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