Trifluoroacetic acid → 4-((3SR,4RS)-4-Acetyl-1-benzyl-pyrrolidin-3-yl)-benzonitrile

HRID 559288Notes

Reaction equation

CO[CH2:3][N:4]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][Si](C)(C)C.[O:17]=[C:18]([CH3:29])/[CH:19]=[CH:20]/[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:18]([CH:19]1[CH2:3][N:4]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:5][CH:20]1[C:21]1[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=1)(=[O:17])[CH3:29]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of N-(methoxymethyl)-N-(phenylmethyl)-N-(trimethylsilyl)methylamine (22.46 g, 94.6 mmol) in CH2Cl2 (100 mL) was added dropwise, over a 30 minutes period, to a stirred solution of 4-((E)-3-oxo-but-1-enyl)-benzonitrile (10.8 g, 63.1 mmol) and trifluoroacetic acid (0.48 mL, 6.30 mmol) in CH2Cl2 (40 mL) at 0° C. The ice bath was removed, and the solution was stirred at 25° C. for an additional 48 h. It was then concentrated and purification by flash chromatography (SiO2, EtOac/Heptane 1:1) afforded 6.3 g (33%) of the title compound as a yellow oil. ES-MS m/e: 305.1 (M+H+).

Workup

customThe ice bath was removed
concentrationIt was then concentrated
custompurification by flash chromatography (SiO2, EtOac/Heptane 1:1)

Sources & evidence

ORD record: ord-40b481b169e94a9c823c1bf64d8c6c80
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063075B2

Reaction notes

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