Trifluoroacetic acid → Methyl 1-benzyl-2,5-dihydro-1H-pyrrole-3-carboxylate

HRID 626938Notes

Reaction equation

[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:21][CH3:22])(=[O:20])[C:18]#[CH:19].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]1[CH2:9][CH:19]=[C:18]([C:17]([O:21][CH3:22])=[O:20])[CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of benzyl(methoxymethyl)[(trimethylsilyl)methyl]amine (7.3 g, 0.03 mol) and methyl prop-2-ynoate (3.1 mL, 0.04 mol) in dichloromethane (150 mL) at 0° C. under nitrogen was added dropwise a solution of trifluoroacetic acid (0.12 mL, 0.002 mol) in dichloromethane (1 mL). The reaction mixture was allowed to stir at 0° C. for 20 minutes, then the ice bath was removed and the solution was allowed to warm to room temperature. The solution was stirred at room temperature for 2 h, then the solvent was evaporated. The residue was purified by FCC, eluting with 0-20% ethyl acetate in heptane, to afford the title compound (2.37 g, 29%) as a yellow oil. δH (250 MHz, CDCl3) 7.35-7.15 (5H, m), 6.70 (1H, s), 3.79 (3H, s), 3.75-3.60 (6H, m).

Workup

customthe ice bath was removed
temperatureto warm to room temperature
stirringThe solution was stirred at room temperature for 2 h
customthe solvent was evaporated
customThe residue was purified by FCC
washeluting with 0-20% ethyl acetate in heptane

Sources & evidence

ORD record: ord-00ef427559554af68eddc45d02b7d77f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309243B2

Reaction notes

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