Sodium Azide → 1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2R,4R)-4-azido-1,2-pyrrolidinedicarboxylate
Reaction equation
[CH2:1]([O:8][C:9](=[O:23])[C@H:10]1[CH2:14][C@H:13](Br)[CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:23])[C@H:10]1[CH2:14][C@@H:13]([N:24]=[N+:25]=[N-:26])[CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The bromo benzyl ester 35 (4.67 g, 12.1 mmol) and NaN3 (4.7 g, 72.3 mmol) were suspended in 175 mL DMF. This mixture was subjected to the procedure for the synthesis of 20 ethyl ester, to give 3.73 g (89% crude yield) of a colorless oil which was used directly in subsequent reactions. 1H NMR (CDCl3) δ1.33/1.45 (2s, 9H), 2.18 (m, 1H), 2.48 (m, 1H), 3.48 (m, 1H), 3.71 (m, 1H), 4.14 (m, 1H), 4.35/4.49 (2dd, J=8.7/3.0 Hz, 1H), 5.16 (m, 2H), 7.34 (s, 5H). FAB MS; MH+ calc. for C17H23N4O4 =347.1719, found 347.1726.