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Trifluoroacetic acid → (2S,4R)-(4-Tritylsulfanyl-pyrrolidin-2-yl)-methanol

HRID 431834
ノート
印刷プレビュー

反応式

HRID 431834 の反応式
C(OC([N:8]1[CH2:12][C@H:11]([S:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH2:33][OH:34])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:14]([S:13][C@H:11]1[CH2:12][NH:8][C@H:9]([CH2:33][OH:34])[CH2:10]1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 11271474(2S,4R)-2-hydroxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 11451661(2S,4R)-(4-Tritylsulfanyl-pyrrolidin-2-yl)-methanol収率 111.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To 25.0 g (52.56 mmol) (2S,4R)-2-Hydroxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester in 80 ml CH2Cl2 were added 40 ml TFA at 0° C., and the solution was stirred at RT over night. The solution was concentrated in vacuo, and the residue was redissolved in EtOAc, washed with sat. NaHCO3 solution, brine, and was dried over Na2SO4. 21.98 g (quant.) (2S,4R)-(4-Tritylsulfanyl-pyrrolidin-2-yl)-methanol were isolated as light brown foam.

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was redissolved in EtOAc
  3. washwashed with sat. NaHCO3 solution, brine
  4. dry with materialwas dried over Na2SO4

出典と根拠

ORDレコード
ord-07d9f9abd693436fa9f50059e6d22007
出典データセット
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06660738B2

反応ノート

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