Sodium Azide → tert-butyl (2S,4R)-4-azido-2-[(benzyloxy)methyl]pyrrolidine-1-carboxylate

HRID 412658Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:12][CH2:13][C@@H:14]1[CH2:18][C@H:17](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:16][N:15]1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)C.CN(C)C=O>[N:1]([C@H:17]1[CH2:16][N:15]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[C@H:14]([CH2:13][O:12][CH2:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:18]1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium azide (0.32 g) was added to a solution of tert-Butyl (2S,4S)-2-[(benzyloxy)methyl]-4-[(4-methylphenyl)sulfonyl]oxypyrrolidine-1-carboxylate (1.15 g) [see Preparation 32] in ethanol (20 ml) and dimethylformamide (5 ml). The reaction mixture was heated to 80° C. for 4 hours, after which time the cooled mixture was partitioned between diethyl ether and water. The organic layer was separated and the aqueous extracted twice with diethyl ether, the combined organic layers were dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was azeotroped with dichloromethane to afford tert-butyl (2S,4R)-4-azido-2-[(benzyloxy)methyl]pyrrolidine-1-carboxylate (820 mg) as an oil.

Workup

customafter which time the cooled mixture was partitioned between diethyl ether and water
customThe organic layer was separated
extractionthe aqueous extracted twice with diethyl ether
dry with materialthe combined organic layers were dried over magnesium sulphate
customthe solvent removed under reduced pressure
customThe residue was azeotroped with dichloromethane

Sources & evidence

ORD record: ord-bd888f360c7347f2a214c17af0425286
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562964B1

Reaction notes

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