Hydrochloric Acid → (S)-3-hydroxy-pyrrolidine-1-carboxylic acid 5-hydroxy-adamantan-2-yl ester

HRID 1752309

反応式

HRID 1752309 の反応式
ClC(Cl)(O[C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.[C:13]12([OH:24])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15](C3O)[CH2:14]1)[CH2:20]2.[OH:25][C@H:26]1[CH2:30][CH2:29][NH:28][CH2:27]1.Cl>ClCCl.N1C=CC=CC=1>[OH:24][C:13]12[CH2:14][CH:15]3[CH2:21][CH:19]([CH2:18][CH:17]([CH:7]3[O:6][C:5]([N:28]3[CH2:29][CH2:30][C@H:26]([OH:25])[CH2:27]3)=[O:11])[CH2:22]1)[CH2:20]2

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 94429TriphosgeneHCID 2733874(3S)-pyrrolidin-3-olHCID 4252005Adamantane-1,4-diol

生成物 1

HCID 58171511(S)-3-hydroxy-pyrrolidine-1-carboxylic acid 5-hydroxy-adamantan-2-yl ester

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-10 °C

実験手順

Triphosgene (0.58 g) dissolved in dichloromethane (10 mL) is added dropwise to a solution of adamantane-1,4-diol (1.00 g) and pyridine (10 mL) in dichloromethane (30 mL) cooled to −10° C. The solution is stirred at ca. 0° C. for 2.5 h and then (S)-3-hydroxy-pyrrolidine (0.50 mL) is added. The resulting solution is stirred overnight while warming to room temperature. The solution is then diluted with dichloromethane (50 mL) and chilled in an ice bath. 4 M hydrochloric acid (25 mL) is added and the resulting mixture is stirred for 5 min. The organic phase is separated and washed with 4 M hydrochloric acid and water. The organic phase is dried (MgSO4) and concentrated to give the title compound as a mixture of diastereomers (ca. 1:1). Yield: 0.98 g (59% of theory); Mass spectrum (ESI+): m/z=282 [M+H]+.

後処理

  1. stirringThe resulting solution is stirred overnight
  2. temperaturewhile warming to room temperature
  3. temperaturechilled in an ice bath
  4. stirringthe resulting mixture is stirred for 5 min
  5. customThe organic phase is separated
  6. washwashed with 4 M hydrochloric acid and water
  7. dry with materialThe organic phase is dried (MgSO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-aa4f94b162ee4f46bfbaeb81dc283bc1
出典データセット
uspto-grants-2015_10
特許番号
US09163012B2

関連ノート

読み込み中…