Hydrochloric Acid → HCID 86637108, compound

HRID 1879256Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:15][C@H:16]3[CH2:20][N:19](C(OC(C)(C)C)=O)[C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.O1CCOCC1.[ClH:38]>>[Cl-:38].[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:15][C@H:16]3[CH2:20][NH2+:19][C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 58005107HCID 58005107, compound

Product 1

HCID 86637108HCID 86637108, compound

Procedure

1-tert-Butyl 2-methyl (2S,4R)-4-[(3′-bromobiphenyl-3-yl)methoxy]pyrrolidine-1,2-dicarboxylate 96 (1.0 eq.) was dissolved at 0° C. in a 4M solution of HCl in dioxane (3.0 eq.) to give a 1.0 M solution. The reaction mixture was stirred at RT for 2 h then the solvent was evaporated under reduced pressure to afford the title compound 97 as a white foam (96%). 1H NMR (400 MHz, DMSO-d6, 300 K) δ 10.33-9.33 (bs, 1H), 7.89 (s, 1H), 7.77-7.71 (m, 2H), 7.67 (d, J 7.7, 1H), 7.62 (d, J 7.7, 1H), 7.54-7.43 (m, 3H), 4.63 (s, 2H), 4.55 (dd, J 10.7, 7.4 Hz, 1H), 4.41 (bs, 1H), 3.81 (s, 3H), 3.51-3.40 (m, 2H), 2.59-2.51 (m, 1H), 2.27-2.16 (m, 1H). MS (ES) m/z 390, 392 (M+H)+.

Sources & evidence

ORD record: ord-09c0412cb1be471f9b88436b380349cd
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314062B2

Reaction notes

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