Triethylamine → (R)-(-)-1-CBZ-3-pyrrolidinol

HRID 50133

反応式

HRID 50133 の反応式
[OH:1][C@@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C(Cl)Cl>[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:3]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 2759337(R)-3-Pyrrolidinol

生成物 1

HCID 11183628(R)-(-)-1-CBZ-3-pyrrolidinol収率 62%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

3-Hydroxy-(R)-pyrrolidine (8.71 g, 0.1 mol) was dissolved in CH2Cl2 (260 mL) and cooled to 0° C. Triethylamine (33.5 mL, 0.24 mol) and benzyl chloroformate (14.9 mL, 0.11 mol) were added, and the resulting solution was stirred for 2 h at 0° C. The solution was gradually warmed to room temperature and allowed to stir overnight. The solution was washed with 1 M HCl, saturated NaHCO3, and brine. The organic solution was dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with ethyl acetate to afford 13.7 g (62% yield, 2 steps) of the desired product as a purple oil.

後処理

  1. temperatureThe solution was gradually warmed to room temperature
  2. stirringto stir overnight
  3. washThe solution was washed with 1 M HCl, saturated NaHCO3, and brine
  4. dry with materialThe organic solution was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-a01212e745274677b3fc30716fa73a7a
出典データセット
uspto-grants-2004_03
特許番号
US06710186B2

関連ノート

読み込み中…