trans-Benzyl 3-(tert-butoxycarbonylamino)-4-fluoropyrrolidine-1-carboxylate → tert-Butyl ((3R,4R)-4-fluoropyrrolidin-3-yl)carbamate

HRID 928195ノート

反応式

HRID 928195 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:13]([F:14])[CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[F:14][C@@H:13]1[CH2:12][NH:11][CH2:10][C@H:9]1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4]

参加物

4

反応物 1

HCID 118084929trans-Benzyl 3-(tert-butoxycarbonylamino)-4-fluoropyrrolidine-1-carboxylate

生成物 1

HCID 58006941tert-Butyl ((3R,4R)-4-fluoropyrrolidin-3-yl)carbamate収率 89%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a solution of (3R,4R)-benzyl 3-((tert-butoxycarbonyl)amino)-4-fluoropyrrolidine-1-carboxylate (3.0 g, 8.8 mmol) in MeOH (50 mL) was added wet Pd/C (0.3 g, 10%) under nitrogen. The suspension was degassed under vacuum and purged with hydrogen three times. The resulting mixture was stirred at rt under hydrogen balloon for 3 hr. The reaction mixture was filtered and the filtrate was concentrated to afford the title compound (1.6 g, 88% yield) as light yellow oil that solidified on standing.

後処理

  1. customThe suspension was degassed under vacuum
  2. custompurged with hydrogen three times
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-9c708ef449754d64962de28bb1b2c5b6
出典データセット
uspto-grants-2016_03
特許番号
US09290496B2

反応ノート

読み込み中…