Benzyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate → Benzyl 5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-cyanophenoxy)-propyl]hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

HRID 857175Notes

Reaction equation

[C:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][C@@H:9]2[CH2:11][N:10]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:5][CH:4]=1)#[N:2].[CH2:21]1[CH:25]2[CH2:26][NH:27][CH2:28][CH:24]2[CH2:23][N:22]1[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>C(O)(C)C>[C:15]([O:14][C:12]([NH:10][C@H:9]([CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:20][CH:19]=1)[CH2:11][N:27]1[CH2:26][CH:25]2[CH2:21][N:22]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:30])[CH2:23][CH:24]2[CH2:28]1)=[O:13])([CH3:16])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 56 °C

Procedure

tert-Butyl (2S)-2-[(4-cyanophenoxy)methyl]aziridine-1-carboxylate (2.5 g, 9.1 mmol; see step (f) above) and benzyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (2.24 g, 9.1 mmol; see step (h) above) was dissolved in isopropanol (30 mL) and was stirred at 56° C. for 24 h. The solvent was then evaporated. The product was purified by chromatography on silica (ethyl acetate, 0–5% MeOH eluant), giving 3.8 g (80%) of the sub-title compound.

Workup

customThe solvent was then evaporated
customThe product was purified by chromatography on silica (ethyl acetate, 0–5% MeOH eluant)

Sources & evidence

ORD record: ord-0a5b0a0085574dafb4f2dba540eb63b9
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144914B2

Reaction notes

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