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

HRID 1752309

반응식

HRID 1752309 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매3회

반응 조건

온도
-10 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-aa4f94b162ee4f46bfbaeb81dc283bc1
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163012B2

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