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

HRID 132820ノート

反応式

HRID 132820 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5d8791d20b284e54b14e8f9856777282
出典データセット
uspto-grants-2008_06
特許番号
US07388095B2

反応ノート

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