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

HRID 1454268Notes

Reaction equation

HRID 1454268 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

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 147726801-Tert-butyl 2-methyl 4-(methanesulfonyloxy)pyrrolidine-1,2-dicarboxylateHCID 21226206Ethyl acetate hexane

Product 1

HCID 147726831-Tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 60EC 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

  1. temperatureThe reaction was then heated to 60EC for 48 h
  2. extractionthe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with sat NaHCO3 and brine
  4. dry with materialthen dried over MgSO4
  5. filtrationThe solution was filtered
  6. customthe solvent removed under reduced pressure
  7. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-13e2dac1c49642f7bfe547af9515d8ac
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

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