Dimethyl Sulfoxide → tert-Butyl 3-(2'-cyano-5-(methoxycarbonyl)-4'-methylbiphenyl-3-yloxy)-4-hydroxypyrrolidine-1-carboxylate

HRID 1845328Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:11]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[CH:31]12[O:36][CH:35]1[CH2:34][N:33]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:32]2>CCOC(C)=O>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:13]=[C:14]([O:16][CH:35]2[CH:31]([OH:36])[CH2:32][N:33]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:34]2)[CH:15]=1)#[N:2]

Participants

Conditions

Temperature: 135 °C

Procedure

A stirred mixture of methyl 2′-cyano-5-hydroxy-4′-methylbiphenyl-3-carboxylate (300 mg, 1.1 mol), potassium carbonate (320 mg, 2.4 mmol), DMSO (8 mL), and tert-butyl 6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylate (2.4 mmol) (J. Am. Chem. Soc. 2008, 130, 3900) was heated at 135° C. overnight. After cooling, the reaction mixture was diluted with EtOAc. The organic phase was washed with aq. NaHCO3 (sat.), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (0-50% EtOAc/hexane) to afford the title compound.

Workup

temperatureAfter cooling
washThe organic phase was washed with aq. NaHCO3 (sat.)
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography (0-50% EtOAc/hexane)

Sources & evidence

ORD record: ord-39ccea92babd476d842cddeee0b2e679
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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