(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine → tert-butyl (S)-1-(2-((trans)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropylamino)ethyl)pyrrolidin-3-ylcarbamate

HRID 535804ノート

反応式

HRID 535804 の反応式
Cl[CH2:2][CH2:3][NH:4][C@@H:5]1[CH2:7][C@H:6]1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[CH:10][CH:9]=1.[NH:24]1[CH2:28][CH2:27][C@H:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25]1>CN(C=O)C>[F:21][C:20]([F:23])([F:22])[C:16]1[CH:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([C@@H:6]3[CH2:7][C@H:5]3[NH:4][CH2:3][CH2:2][N:24]3[CH2:28][CH2:27][C@H:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:25]3)=[CH:9][CH:10]=2)[CH:19]=[CH:18][CH:17]=1

参加物

4

反応物 2

HCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 89123862(trans)-N-(2-chloroethyl)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropanamine

生成物 1

HCID 86673372tert-butyl (S)-1-(2-((trans)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropylamino)ethyl)pyrrolidin-3-ylcarbamate収率 37%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (trans)-N-(2-chloroethyl)-2-(3′-(trifluoromethyl)biphenyl-4-yl)cyclopropanamine (750 mg, 2.21 mmol) in dry DMF (7.5 mL), (S)-tert-butyl pyrrolidin-3-ylcarbamate (864 mg g, 4.64 mmol) was added and stirred at RT for 48 h. After completion, the reaction mixture was poured into ice water (25 mL), extracted with EtOAc (2×20 mL). The combined extracts were washed with water (25 mL), brine (20 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by column chromatography (SiO2) using MeOH: CHCl3(4:96) to get tert-butyl (S)-1-(2-((trans)-2-(3′-(trifluoromethyl)biphenyl-4-yl)cyclopropylamino)ethyl)pyrrolidin-3-ylcarbamate (400 mg, 37%) as a white solid.

後処理

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined extracts were washed with water (25 mL), brine (20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude residue was purified by column chromatography (SiO2)

出典と根拠

ORDレコード
ord-8c29d5dc90f64551bb0ac83e0d7cfd57
出典データセット
uspto-grants-2014_10
特許番号
US08859555B2

反応ノート

読み込み中…