Ethyl Acetate → (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-(t-butyldimethylsilyloxy) pyrrolidine

HRID 975695Notes

Reaction equation

[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][C@H:8]1[CH2:20][CH2:21]OS(C)(=O)=O)=[O:6])[CH:2]=[CH2:3].[Cl-].[NH4+].[N-:29]=[N+:30]=[N-:31].[Na+].C(OCC)(=O)C>CN(C)C=O.O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][C@H:8]1[CH2:20][CH2:21][N:29]=[N+:30]=[N-:31])=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(2-methanesulfonyloxyethyl) pyrrolidine (37.6 g) and ammonium chloride (5.84 g) in dimethylformamide (185 ml) was added portionwise sodium azide (7.1 g) at ambient temperature. The mixture was stirred at 70° C. for 3 hours, and poured into a mixture of ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed twice with water and once with brine, dried over magnesium sulfate and evaporated under reduced pressure to give (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-(t-butyl-dimethylsilyloxy) pyrrolidine (29.7 g).

Workup

customThe organic layer was separated
extractionthe aqueous layer was extracted twice with ethyl acetate
washThe combined organic layer was washed twice with water and once with brine
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-00d0c27ed4db4023802269256e535eff
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05608056

Reaction notes

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