Bromoacetonitrile → Ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate

HRID 1501838Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[CH2:31][C:32]#[N:33]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:31][C:32]#[N:33])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Into a 250-mL 3-necked round-bottom flask was placed a solution of ethyl 1-benzyl-3-oxopiperidine-4-carboxylate (10 g, 38.27 mmol, 1.00 equiv) in tetrahydrofuran (80 mL). This was followed by the addition of a solution of KHMDS in tetrahydrofuran (42 mL, 1M) dropwise with stirring at 0° C., and 30 min later, 2-bromoacetonitrile (6.89 g, 57.44 mmol, 1.50 equiv) was added dropwise with stirring at 0° C. The resulting solution was stirred for 4 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether to give the title compound.

Workup

customInto a 250-mL 3-necked round-bottom flask was placed
stirringwith stirring at 0° C
stirringThe resulting solution was stirred for 4 h at room temperature
concentrationThe resulting mixture was concentrated under vacuum
washeluted with ethyl acetate/petroleum ether

Sources & evidence

ORD record: ord-a9ba9fd918bb4f6ca535c782bee52992
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206198B2

Reaction notes

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