Sodium Azide → HCID 92019678, compound

HRID 877712Notes

Reaction equation

HRID 877712 reaction equation
[CH3:1][O:2][C@H:3]1[C@H:7](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:6][N:5]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:4]1.[N-:29]=[N+:30]=[N-:31].[Na+]>O.CN(C=O)C.CC(=O)OCC.O>[N:29]([C@H:7]1[C@@H:3]([O:2][CH3:1])[CH2:4][N:5]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:6]1)=[N+:30]=[N-:31]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 131732606HCID 131732606, compound

Product 1

HCID 92019678HCID 92019678, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Procedure

(+/−)-Trans-benzyl 3-methoxy-4-(tosyloxy)pyrrolidine-1-carboxylate (10.3 g, 25.4 mmol) was added to the soln. of sodium azide (5.78 g, 89 mmol) in water (10 mL) and DMF (60 mL) and heated to 100 deg. Celsius overnight. Diluted with EA/water and stirred. The organic layer dried (Na2SO4) and concentrated to give (+/−)-Cis-benzyl 3-azido-4-methoxypyrrolidine-1-carboxylate (6.3 g, 22.80 mmol, 90% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 7.34-7.43 (5 H, m), 5.13-5.21 (2 H, m), 4.01-4.04 (2 H, m), 3.47 (3 H, s), 3.49-3.69 (4 H, m), Hz), LCMS: M+23=299, Rt=2.15 min.

Workup

  1. dry with materialThe organic layer dried (Na2SO4)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5e497ef00c1c4558bcbcc53325318520
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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