Sodium Azide → 1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2R,4R)-4-azido-1,2-pyrrolidinedicarboxylate

HRID 893060Notes

Reaction equation

HRID 893060 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]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 14842661HCID 14842661, compound

Product 1

HCID 148426651-(1,1-Dimethylethyl) 2-(phenylmethyl) (2R,4R)-4-azido-1,2-pyrrolidinedicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. customto give 3.73 g (89% crude yield) of a colorless oil which

Sources & evidence

ORD record
ord-bc110bcf350342a5a1687ed22376a67d
Source dataset
uspto-grants-1992_06
Patent number
US05120859

Reaction notes

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