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

HRID 132820Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-5d8791d20b284e54b14e8f9856777282
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07388095B2

Reaction notes

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