Methyl propiolate → HCID 118235742, compound

HRID 626945Notes

Reaction equation

CO[CH2:3][N:4]([CH2:13][Si](C)(C)C)[C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6].[C:18]([O:22][CH3:23])(=[O:21])[C:19]#[CH:20]>ClCCl.FC(F)(F)C(O)=O>[C:7]1([C@H:5]([N:4]2[CH2:3][CH:20]=[C:19]([C:18]([O:22][CH3:23])=[O:21])[CH2:13]2)[CH3:6])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (1R)-N-(methoxymethyl)-1-phenyl-N-[(trimethylsilyl)-methyl]ethanamine (55.83 mL, 205.62 mmol) and methyl prop-2-ynoate (22.5 mL, 252.9 mmol) in dichloromethane (500 mL) at 0° C. under nitrogen was added trifluoroacetic acid (800 μL, 10.45 mmol). 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 1 h. The reaction mixture was concentrated to dryness and the residue was purified by FCC, eluting with 0-70% EtOAc in heptane, to afford the title compound (26.5 g, 56%) as a yellow oil. δH (500 MHz, CDCl3) 7.41-7.29 (m, 4H), 7.28-7.21 (m, 1H), 6.77-6.70 (m, 1H), 3.72 (s, 3H), 3.71-3.65 (m, 1H), 3.65-3.42 (m, 4H), 1.40 (d, J 6.6 Hz, 3H). Method F HPLC-MS: MH+ m/z 232, RT 1.62 minutes.

Workup

customthe ice bath was removed
temperatureto warm to room temperature
stirringThe solution was stirred at room temperature for 1 h
concentrationThe reaction mixture was concentrated to dryness
customthe residue was purified by FCC
washeluting with 0-70% EtOAc in heptane

Sources & evidence

ORD record: ord-ee4b7375766b43ef94f606f5eaf9f045
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309243B2

Reaction notes

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