Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate → tert-Butyl 5-[(2S)-3-(4-cyanophenoxy)-2-hydroxypropyl]hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

HRID 857182Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

4-[(2S)-Oxiranylmethoxy]benzonitrile (4.36 g, 0.025 mol; prepared as described in International Patent Application WO 99/31100) and tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (6.2 g, 0.025 mol; see Preparation A above) were mixed in isopropanol and stirred at 60° C. overnight. The solvent was evaporated and the product was purified by flash chromatography on silica, eluting with ethyl acetate, 10% MeOH. This gave 1.2 g (88%) of the sub-title compound.

Workup

customPreparation A above)
customThe solvent was evaporated
customthe product was purified by flash chromatography on silica
washeluting with ethyl acetate, 10% MeOH

Sources & evidence

ORD record: ord-2036e5b00be548eb9b0770fa656cf707
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144914B2

Reaction notes

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