Water → Benzyl (3S,4S)-3-(Allyloxy)-4-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylate

HRID 1173199Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]1[CH:13]([OH:14])[CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:27](Br)[CH:28]=[CH2:29].O>C1COCC1>[CH2:29]([O:14][C@@H:13]1[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:10][N:11]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:12]1)[CH:28]=[CH2:27]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 26 g (77 mmol) of benzyl 3-[(tert-butoxycarbonyl)amino]4-hydroxypyrrolidine-1-carboxylate in 120 mL of THF was added 5 g (211 mmol) of sodium hydride at 0° C. The reaction mixture was stirred at 0° C. for 1 h, then 10 mL (115 mmol) of allyl bromide was added. The reaction mixture was warmed up to room temperature and continuously stirred at room temperature overnight. Water (50 mL) was added to quench the reaction. The organic phase was separated, and the aqueous layer was extracted with ethyl acetate twice (100 mL×2). The combined extracts were washed with brine, dried over Na2SO4, evaporated under reduced pressure. Chromatography on silica gel column with 25% EtOAc-hexane provided the title compound (21.3 g, 73%). MS (M+H)+ 377.

Workup

temperatureThe reaction mixture was warmed up to room temperature
stirringcontinuously stirred at room temperature overnight
customto quench
customthe reaction
customThe organic phase was separated
extractionthe aqueous layer was extracted with ethyl acetate twice (100 mL×2)
washThe combined extracts were washed with brine
dry with materialdried over Na2SO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-1036079f938f46e4afcaee2de456a1e0
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834021B2

Reaction notes

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