HCID 58055039, compound → HCID 68026894, compound

HRID 2383505Notes

Reaction equation

[C:1](=[O:19])([O:12][C@@H:13]([CH3:18])[C:14]([F:17])([F:16])[F:15])OC1C=CC([N+]([O-])=O)=CC=1.[CH3:20][O:21][C@:22]12[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][C@H:23]1[NH:24][CH2:25][CH2:26]2>C(Cl)(Cl)Cl>[CH3:20][O:21][C@:22]12[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][C@H:23]1[N:24]([C:1]([O:12][C@@H:13]([CH3:18])[C:14]([F:15])([F:16])[F:17])=[O:19])[CH2:25][CH2:26]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-nitrophenyl (2S)-1,1,1-trifluoropropan-2-yl carbonate (15 mg) prepared in Referential Example 2 in CHCl3 (2 mL) was added tert-butyl (3aR,6aR)-3a-methoxyhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (11 mg) at room temperature. The resulting mixture was stirred at 100° C. in a sealed tube for 2 hours and then cooled to room temperature. The mixture was purified with silica gel column chromatography (eluent: hexane/EtOAc=1/0˜0/1) to give 5-tert-butyl 1-[(2S)-1,1,1-trifluoropropan-2-yl] (3aR,6aR)-3a-methoxyhexahydropyrrolo[3,4-b]pyrrole-1,5-dicarboxylate as a pale yellow foam.

Workup

temperaturecooled to room temperature
customThe mixture was purified with silica gel column chromatography (eluent: hexane/EtOAc=1/0˜0/1)

Sources & evidence

ORD record: ord-e71e6c52981e469bab699592fe4b0724
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263632B2

Reaction notes

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