Water → 4-Azido-2-methoxymethyl-pyrrolidine-1-carboxylic Acid T-butyl Ester

HRID 1071493Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH:9]1[CH2:18][O:19][CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:21]=[N+:22]=[N-:23].[Na+].O.CCCCCC.C(OCC)(=O)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([N:21]=[N+:22]=[N-:23])[CH2:10][CH:9]1[CH2:18][O:19][CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

The 4-methanesulfonyloxy-2-methoxymethyl-pyrrolidine-1-carboxylic acid t-butyl ester (172.26 mg, 0.56 mmol) was taken up in dry DMF under argon and sodium azide (182.00 mg, 2.80 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 122.00 mg. C11H22N2O3 MS m/e=257.3 (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-d5a3bc4ce2c14225bbf9dd2e2c11e5bf
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06906067B2

Reaction notes

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