Hydrochloric Acid → (3R,5S)-5-(Methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate Hydrochloride

HRID 2045701Notes

Reaction equation

HRID 2045701 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([C:12]([O:14][C@H:15]1[CH2:19][N:18](C(OC(C)(C)C)=O)[C@H:17]([C:27]([O:29][CH3:30])=[O:28])[CH2:16]1)=[O:13])[CH2:7]2)=[CH2:2].[ClH:31]>CCOC(C)=O>[ClH:31].[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([C:12]([O:14][C@@H:15]1[CH2:16][C@@H:17]([C:27]([O:29][CH3:30])=[O:28])[NH:18][CH2:19]1)=[O:13])[CH2:7]2)=[CH2:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 453783721-t-Butyl 2-methyl (2S,4R)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboxylate

Product 1

HCID 45379932(3R,5S)-5-(Methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate HydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-tert-Butyl 2-methyl (2S,4R)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboxylate (13.9 g, 33.4 mmol) in EtOAc (700 mL) was cooled in an ice bath the saturated with HCl gas. The reaction flask was sealed and allowed to warm to RT. After 3.5 h, the solvent was removed by evaporation to give the title compound as a gray solid, 11.2 g, 95% yield). 1H NMR (500 MHz, CD3OD) δ 7.47-7.45 (m, 1H), 7.32-7.31 (m, 1H), 7.26-7.21 (m, 1H), 6.79-6.73 (m, 1H), 5.79-5.73 (m, 1H), 5.46 (s, 1H), 5.41-5.38 (m, 1H), 4.80-4.72 (m, 4H), 3.91 (s, 3H), 3.74-3.63 (m, 2H), 2.77-2.71 (m, 1H), 2.51-2.46 (m, 1H). LRMS (ESI) m/z 317 [(M+H)+; calcd for C17H21N2O4: 317].

Workup

  1. customThe reaction flask was sealed
  2. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-f4f6e05d06284bc68923faff0019ce76
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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