Trimethylsilyl triflate → Benzyl 2,3-dihydro-1H-pyrrole-1-carboxylate

HRID 132820노트

반응식

HRID 132820 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1OC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH:12]=[CH:13][CH2:14][CH2:15]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 65367Trimethylsilyl triflateHCID 109224852-Methoxy-pyrrolidine-1-carboxylic acid benzyl ester

생성물 1

HCID 11074472Benzyl 2,3-dihydro-1H-pyrrole-1-carboxylate수율 75.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a cold (0° C.) solution of 2-methoxy-pyrrolidine-1-carboxylic acid benzyl ester (example 4, step 4, 500 mg, 1.0 eq.) in dichloromethane was added N-diisopropylethyl-amine (0.5 mL, 1.36 eq.) and trimethylsilyltrifluoromethanesulfonate (0.51 mL, 1.3 eq.). The reaction mixture was stirred at 0° C. for 30 min and partitioned between dichloromethane and an aqueous solution of sodium hydrogencarbonate. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water and evaporated in vacuo and purified on silica eluting with 19:1 cyclohexane/ethyl acetate to yield 325 mg (75%) of the desired product as a colourless oil. MS (m/e): 204.5 (MH+, 100%).

후처리

  1. custompartitioned between dichloromethane
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with water
  4. customevaporated in vacuo
  5. custompurified on silica eluting with 19:1 cyclohexane/ethyl acetate

출처 및 근거

ORD 기록
ord-5d8791d20b284e54b14e8f9856777282
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388095B2

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