Acetic Acid → (2S,4S)-4-azido-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester

HRID 1527900ノート

反応式

HRID 1527900 の反応式
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]([C@@H:12]1[CH2:16][C@H:15]([N:17]=[N+:18]=[N-:19])[CH2:14][NH:13]1)=[O:11].[CH:20]1([CH:26]=O)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:8][O:9][C:10]([C@@H:12]1[CH2:16][C@H:15]([N:17]=[N+:18]=[N-:19])[CH2:14][N:13]1[CH2:26][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:11]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 16275CyclohexanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 89768308(2S,4S)-4-azido-pyrrolidine-2-carboxylic acid methyl ester trifluoro-acetate salt

生成物 1

HCID 117774177(2S,4S)-4-azido-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester収率 177.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (2S,4S)-4-azido-pyrrolidine-2-carboxylic acid methyl ester trifluoroacetate salt (9.6 g, 33.08 mmol) in 60 mL dichloromethane were added cyclohexanecarbaldehyde (2.6 g, 23.66 mmol), acetic acid (2.5 mL) and sodium triacetoxyborohydride (14.2 g, 66.16 mmol) and the reaction mixture was stirred at room temp. for 20 h. The reaction mixture was diluted with dichloromethane, washed with water, dried over anhydrous sodium sulfate and concentrated to give (2S,4S)-4-azido-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester (11.2 g, crude) as a light brown liquid. The compound was used in the next step without further purification. MS calcd. for C13H23N4O2 [(M+H)+] 267.0, obsd. 267.2.

後処理

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-80145308ba7242e5a2b55b86654ca98c
出典データセット
uspto-grants-2015_07
特許番号
US09090559B2

反応ノート

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