Potassium hydroxy sulfite → 3-[4-(2-Cyano-benzenesulfinyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 503935노트

반응식

HRID 503935 반응식
[OH:1]OS([O-])=O.[K+].[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])=[CH:21][C:20]=2[O:34][CH3:35])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>O.CO.C(#N)C>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])=[O:1])=[CH:21][C:20]=2[O:34][CH3:35])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

참가 물질

6

반응물 2

HCID 23707502Potassium hydroxy sulfiteHCID 594284293-[4-(2-Cyano-phenylsulfanyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 668771343-[4-(2-Cyano-benzenesulfinyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

A solution of OXONE™ (0.470 g, 0.7636 mmol) in water (5 mL) was added to a solution of 3-[4-(2-cyano-phenylsulfanyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.209 g, 0.5091 mmol) in a mixture of MeOH (5 mL) and acetonitrile (5 mL). The reaction mixture was stirred at room temperature for 3 hours, then water was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (hexane/EtOAc, 7/3) to give 0.215 g of 3-[4-(2-cyano-benzenesulfinyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (not shown in Scheme O) as a clear oil.

후처리

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe resulting crude material was purified via flash chromatography (hexane/EtOAc, 7/3)

출처 및 근거

ORD 기록
ord-d3097b7aa9a34fc6928048ea4c2cf557
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776910B2

반응 노트

불러오는 중…