Benzyl chloroformate → HCID 67357132, 화합물

HRID 627349노트

반응식

HRID 627349 반응식
[CH2:1]([N:9]1[CH2:15][CH2:14][CH2:13][C@@H:12]2[CH2:16][CH2:17][NH:18][C@@H:11]2[CH2:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([O:32][C:33](Cl)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(OCC)(=O)C.O>[CH2:25]([O:32][C:33]([N:18]1[C@@H:11]2[CH2:10][N:9]([CH2:1][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:15][CH2:14][CH2:13][C@@H:12]2[CH2:16][CH2:17]1)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

6

반응물 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 11955366(3aR,8aS)-7-Phenethyl-decahydro-pyrrolo[2,3-c]azepine

생성물 1

HCID 67357132HCID 67357132, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a suspension of (3aR,8aS)-7-Phenethyl-decahydro-pyrrolo[2,3-c]azepine (4.0 g, 16.37 mmol) (Reference: PCT Int. Appl., 2005097791, 20 Oct. 2005) in ethyl acetate (100 mL) was added a solution of potassium carbonate (6.79 g, 49.1 mmol, 3.0 eq) in water (100 mL). The biphasic solution was cooled to 0° C. then benzylchloroformate (2.80 mL, 19.64 mmol, 1.2 eq) added dropwise. The resulting mixture was stirred for 3 hr at 23° C. The mixture was partitioned and the aqueous layer extracted with Ethyl Acetate. The combined organic layers were washed with water followed by brine and the organic layer dried (Na2SO4), filtered, and the filtrate concentrated to yield an orange oil. The crude was purified using silica gel chromatography (1:2 Ethyl Acetate/Heptane to 100% Ethyl Acetate followed by 12:1 CH2Cl2/Methanol) giving (3aR,8aS)-7-Phenethyl-octahydro-pyrrolo[2,3-c]azepine-1-carboxylic acid benzyl ester.

후처리

  1. customThe mixture was partitioned
  2. extractionthe aqueous layer extracted with Ethyl Acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialthe organic layer dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated
  7. customto yield an orange oil
  8. customThe crude was purified

출처 및 근거

ORD 기록
ord-b50e947b76b9473fa63ab52d97fb6307
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309252B2

반응 노트

불러오는 중…