Diisopropylamine → rac-(3S,4R)-[4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

HRID 527470ノート

反応式

HRID 527470 の反応式
[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:11][N:10](CC2C=CC=CC=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(NC(C)C)(C)C.C(OC(Cl)C)=O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 7912DiisopropylamineHCID 153309271-ChloroethylformateHCID 67237396rac-(3S,4R)-[1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

生成物 1

HCID 67237824rac-(3S,4R)-[4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester収率 153%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of rac-(3S,4R)-[1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (5.59 g, 0.013 mol) and N,N-diisopropylamine (6.81 mL, 0.017 mol) in toluene (60 mL) was added at ambient temperature 1-chloroethyl formate (1.88 mL, 0.017 mol) and the reaction mixture was stirred for 24 h. It was concentrated and the resulting residue was diluted in methanol (60 mL) and stirred for 3 h at ambient temperature. Concentration afforded the crude title compound (6.59 g, 67% purity) as a light brown solid which was directly used without further purification.

後処理

  1. concentrationIt was concentrated
  2. additionthe resulting residue was diluted in methanol (60 mL)
  3. stirringstirred for 3 h at ambient temperature
  4. concentrationConcentration

出典と根拠

ORDレコード
ord-adee08ad31424aa8aae613e34fc3fc3c
出典データセット
uspto-grants-2016_05
特許番号
US09346786B2

反応ノート

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