Formaldehyde → HCID 53312154, compound

HRID 924347Notes

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-])([O-])=O.[K+].[K+].C=O>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: 45 °C

Procedure

To a solution of (S)-3-Benzoyl-5-biphenyl-4-ylmethyl-1-((E)-but-1-enyl)-pyrrolidin-2-one (4a, R1=1-butenyl, R4=phenyl) (5.5 g, 13.2 mmol) in 25 mL of tetrahydrofuran is added 1 M K2CO3 aqueous solution (26.4 mL, 26.4 mmol), 37% CH2O aqueous solution (2.2 mL, 26.4 mmol) and n-Bu4NOH (0.4 mL, 0.7 mmol), heat to 45° C. under N2 for 2 h, cool to room temperature, extract with toluene, the combined organic layer are washed with 5% HCl(aq), saturated Na2CO3 aqueous solution and brine, dry over anhydrous Na2SO4, evaporate the solvent, the residue is purified by column chromatography to obtain (R)-5-Biphenyl-4-ylmethyl-1-((E)-but-1-enyl)-3-methylene-pyrrolidin-2-one (1a, R1=1-butenyl). Spectroscopic data as Example 24, Method 1.

Workup

temperaturecool to room temperature
extractionextract with toluene
washthe combined organic layer are washed with 5% HCl(aq), saturated Na2CO3 aqueous solution and brine
dry with materialdry over anhydrous Na2SO4
customevaporate the solvent
customthe residue is purified by column chromatography

Sources & evidence

ORD record: ord-fb69bf9c2ff94064b2da5c60aaa4bec3
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278908B2

Reaction notes

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