Sodium Azide → HCID 57029350, compound

HRID 1034501Notes

Reaction equation

HRID 1034501 reaction equation
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[CH2:16][C@@H:15]([OH:17])[CH2:14][N:13]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[O:19])(=O)=O)=CC=1.[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C)C=O.O>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][O:20][C:18]([N:13]2[CH2:14][C@H:15]([OH:17])[CH2:16][C@H:12]2[CH2:11][N:31]=[N+:32]=[N-:33])=[O:19])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 131718419HCID 131718419, compound

Product 1

HCID 57029350HCID 57029350, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxypyrrolidine-2-methanol p-toluenesulfonate (8.7 g: 20 mmole) in dimethylformamide (60 ml), a solution of sodium azide (1.56 g) in water (6 ml) is added. The mixture is stirred at 80° C. overnight. The reaction mixture is poured into ice water and extracted with ethyl acetate. The extract is successively washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo to give crude (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxy-2-azidomethylpyrrolidine (5.6 g). Yield: 92%. NMR δ(CDCl3) ppm: 1.95 to 2.1(m, 2H), 3.2 to 3.8(m, 3H), 3.81(s, 3H), 3.83 to 4.6(m, 3H), 5.07(s, 2H), 6.89(d, J=8.8 Hz, 2H), 7.31(d, J=8.8 Hz, 2H). IR ν (CHCl3) cm-1 : 3420, 2100, 1689.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is successively washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ffae74474524b6f991d61d963bc37aa
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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