Formic Acid → (3aRS,4RS,6aSR)-2-benzyl-4-(4-bromobenzyl)-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione

HRID 2293300Notes

Reaction equation

[CH2:1]([N:8]1[C:15](=[O:16])[CH:14]2[CH:10]([C:11]([CH3:26])([CH3:25])[NH:12][CH:13]2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)[C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28](O)=O.C=O>[OH-].[Na+]>[CH2:1]([N:8]1[C:15](=[O:16])[CH:14]2[CH:10]([C:11]([CH3:25])([CH3:26])[N:12]([CH3:28])[CH:13]2[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([Br:24])=[CH:22][CH:23]=2)[C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3.88 g (9.1 mmol) of (3aRS,4RS,6aSR)-2-benzyl-4-(4-bromo-benzyl)-6,6-dimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione, 85% formic acid (4.9 g, 90 mmol) and 35% formalin solution (2.6 g, 30 mmol) were heated to 100° C. for 5.5 hours. After cooling 1N NaOH (50 ml) was added and the mixture was extracted four times with dichloromethane. The organic phase was concentrated and the residue was separated chromatographically (hexane/ethyl acetate 3:1+1% triethylamine). 3.45 g of (3aRS, 4RS,6aSR)-2-benzyl-4-(4-bromobenzyl)-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione were isolated as a yellowish oil. FAB-MS: 441 ([M+H]+, 40); 271 (100); 212 (5); 169 (11); 136 (14); 110 (26); 91 (42).

Workup

additionwas added
extractionthe mixture was extracted four times with dichloromethane
concentrationThe organic phase was concentrated
customthe residue was separated chromatographically (hexane/ethyl acetate 3:1+1% triethylamine)

Sources & evidence

ORD record: ord-e5a788c2b1f14804b0e297c5aa895b7e
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686459

Reaction notes

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