Formaldehyde → HCID 53312154, compound

HRID 2179531Notes

Reaction equation

[C:1]([C@@H:9]1[CH2:13][CH:12]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[N:11](/[CH:27]=[CH:28]/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:10]1=[O:35])(=O)C1C=CC=CC=1.C=O.C([O-])([O-])=O.[K+].[K+]>O1CCCC1>[C:18]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:17]=[CH:16][C:15]([CH2:14][C@H:12]2[N:11](/[CH:27]=[CH:28]/[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:10](=[O:35])[C:9](=[CH2:1])[CH2:13]2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 40 °C

Procedure

(S)-3-Benzoyl-5-biphenyl-4-ylmethyl-1-((E)-styryl)-pyrrolidin-2-one (4a, R1=styryl, R4=phenyl) (1.0 g, 2.2 mmol) is dissolved in 5 mL of anhydrous tetrahydrofuran, add 37% formaldehyde aqueous solution (0.36 mL, 4.4 mmol), 1 M K2CO3 aqueous solution (4.4 mL, 4.4 mmol) and n-Bu4NOH (12 mg, 0.05 mmol), heat to 40° C. for 2 h. The reaction mixture is cooled to room temperature, extract with ethyl acetate, the extracts are washed with saturated Na2CO3 aqueous solution and brine, dry over anhydrous Na2SO4 and concentrate under vacuum, the residue is purified by column chromatography to obtain (R)-5-Biphenyl-4-ylmethyl-3-methylene-1-((E)-styryl)-pyrrolidin-2-one (1a, R1=styryl). Spectroscopic data as Example 23, Method 1.

Workup

temperatureThe reaction mixture is cooled to room temperature
extractionextract with ethyl acetate
washthe extracts are washed with saturated Na2CO3 aqueous solution and brine
dry with materialdry over anhydrous Na2SO4
concentrationconcentrate under vacuum
customthe residue is purified by column chromatography

Sources & evidence

ORD record: ord-eb103e7ae2b649e4ace3596de270c93e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067883B2

Reaction notes

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