Water → 1-Tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

HRID 1071508Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8](OS(C)(=O)=O)[CH2:7][N:6]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:4].[N-:22]=[N+:23]=[N-:24].[Na+].O.CCCCCC.C(OCC)(=O)C>CN(C=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:22]=[N+:23]=[N-:24])[CH2:7][N:6]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

4-Methanesulfonyloxy-pyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-methyl ester (406.92 mg, 1.26 mmol) was taken up in dry DMF under argon and sodium azide (409.50 mg, 6.30 mmol) was added. The reaction was then heated to 60° C. for 48 h. The reaction was poured into water and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with sat NaHCO3 and brine then dried over MgSO4. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (3:1 hexane-ethyl acetate) Yield 303.10 mg. C11H18N4O4 MS m/e=271.2 (M+H).

Workup

extractionthe aqueous layer was extracted three times with ethyl acetate
washThe combined organic layers were washed with sat NaHCO3 and brine
dry with materialthen dried over MgSO4
filtrationThe solution was filtered
customthe solvent removed under reduced pressure
customThe product was isolated by flash chromatography

Sources & evidence

ORD record: ord-e22f3e1f810c46b59917cfa2cd437f9d
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06906067B2

Reaction notes

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