Water → HCID 22391924, compound

HRID 743480Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[N:6][CH2:7][C:8]1(C)[CH:13]=[CH:12][CH:11]=[CH:10][CH2:9]1)[CH3:2].[CH:16]1[CH2:20][CH:19]=[CH:18][CH:17]=1.[C:21](O)(C(F)(F)F)=O.O>CN(C=O)C>[C:8]1([CH:7]([N:6]2[CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH:20]3[CH2:16][CH:17]2[CH:18]=[CH:19]3)[CH3:21])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of N-[(1-methyl)phenylmethyl]imino-acetic acid ethyl ester (67.5 g; 328.9 mmol) and cyclopentadiene (43.48 g, 657.8 mmol) in dry DMF under argon cooled to 0° C., was added in portions (5 ml portion) 37.5 g (328.9 mmol) of TFA followed by water (0.057 ml) and the resulting mixture was allowed to stir at room temperature for 22 hours. The above reaction mixture was poured into ice, extracted with 80% hexane in ethyl acetate (to remove excess cyclopentadiene), and the aqueous layer was slowly neutralized with sodium bicarbonate (to pH=8). The aqueous layer was extracted with ethyl acetate and the organic layer was separated and dried over sodium sulfate. The organic solvent was concentrated in vacuo to afford 52.6 g (62%) of ethyl 2-(1-phenylethyl)-2 -azabicyclo [2,2,1 ]hept-5-en-3-carboxylate.

Workup

customThe above reaction mixture
additionwas poured into ice
extractionextracted with 80% hexane in ethyl acetate (to remove excess cyclopentadiene)
extractionThe aqueous layer was extracted with ethyl acetate
customthe organic layer was separated
dry with materialdried over sodium sulfate
concentrationThe organic solvent was concentrated in vacuo

Sources & evidence

ORD record: ord-e0dd3484873e4d4fb6da13b0fa73329d
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556909

Reaction notes

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