Benzyl 2,5-dioxopyrrolidine-1-carboxylate → trans-Benzyl 3-hydroxycyclopentylcarbamate

HRID 271370ノート

反応式

HRID 271370 の反応式
[OH:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH2:7])[CH2:3]1.[CH2:8]([O:15][C:16](N1C(=O)CCC1=O)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(#N)C>[OH:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:16](=[O:17])[O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1

参加物

4

反応物 2

HCID 3826287Benzyl 2,5-dioxopyrrolidine-1-carboxylateHCID 42614395(1S,3S)-3-Aminocyclopentan-1-ol

生成物 1

HCID 59834849trans-Benzyl 3-hydroxycyclopentylcarbamate収率 981.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of crude trans-3-hydroxycyclopentanamine (0.42 g, 4.2 mmol) and N-(benzyloxycarbonyl)succinimide (1.05 g, 0.42 mmol) in acetonitrile (40 ml) was stirred at ambient temperature under nitrogen for 18 hours. The mixture was concentrated under reduced pressure. The residue was taken up in ethyl acetate (150 ml), washed with water (3×75 ml), and brine (50 ml), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure to give benzyl (trans-3-hydroxycyclopentyl)carbamate (0.97 g, 98%), as a white solid.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washwashed with water (3×75 ml), and brine (50 ml)
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

出典と根拠

ORDレコード
ord-fb46d788fc814cb2ad333ca1dcf47da3
出典データセット
uspto-grants-2008_11
特許番号
US07452893B2

反応ノート

読み込み中…