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

HRID 2377604Notes

Reaction equation

HRID 2377604 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].O1CCOCC1>>[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

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 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 98.4%

Procedure

A mixture of 1-t-butyl 2-methyl (2S,4R)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboxylate (18.0 g, 43.2 mmol) and HCl/dioxane (4 M) (43.2 mL, 173 mmol) was stirred at RT for 2h. The reaction mixture was concentrated to remove the dioxane followed by concentration from Et2O to give (3R,5S)-5-(methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate hydrochloride as an off-white solid (15 g) which was used without further purifcation. LRMS (ESI) m/z 317 [(M+H)+; calcd for C17H21N2O4: 317].

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove the dioxane
  3. concentrationfollowed by concentration from Et2O

Sources & evidence

ORD record
ord-d88a4b0691a845c1bb87b90662578131
Source dataset
uspto-grants-2008_12
Patent number
US07470664B2

Reaction notes

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