Sodium Azide → (3S)-3-azido-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

HRID 891720Notes

Reaction equation

CS(O[C@@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[CH2:7]1)(=O)=O.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C)C=O>[N:24]([C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[CH2:7]1)=[N+:25]=[N-:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (3R)-3-methanesulfonyloxy-1-(p-nitrobenzyloxycarbonyl)-pyrrolidine (4.00 g, 11.6 mmol) (obtained as described in Reference Example 52(2)) in dimethylformamide (120 ml) was added sodium azide (831 mg, 12.8 mmol), and the mixture was stirred in an oil bath (100° C.) for 2 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (3:1→1:2) as the eluant to afford (3S)-3-azido-1-(p-nitrobenzyloxycarbonyl)pyrrolidine (3.43 g, yield 100%) as a pale yellow solid.

Workup

customthe completion of the reaction
customthe reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
washThe organic layer was washed with saturated aqueous sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record: ord-a5a3f949d0fd4768afeca4b3ed6b60e1
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001897B2

Reaction notes

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