Water → HCID 19705530, compound

HRID 727574Notes

Reaction equation

HRID 727574 reaction equation
[N:1]([CH2:4][CH2:5][CH:6]([C:14]1([C:28]([CH3:30])=[CH2:29])[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]1=[O:27])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][CH2:5][CH:6]([C:14]1([C:28]([CH3:30])=[CH2:29])[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]1=[O:27])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 19705496HCID 19705496, compound

Product 1

HCID 19705530HCID 19705530, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl α-(2-azidoethyl)-2-oxo-1-(2-phenylethyl)-3-(propen-2-yl)-3-pyrrolidineacetate (2.12 g, 5.14 mmol) and triphenylphosphine (1.48 g, 5.65 mmol) in THF (15 mL) is stirred under N2 for 7 hours. Water (1 mL) is added and the solution stirred overnight at room temperature under N2. The solution is concentrated and purified by silica gel chromatography (75 g SG; EtOAc, 20% MeOH/EtOAc) to provide 1.94 g (97%) of the title compound as a yellow oil:

Workup

  1. concentrationThe solution is concentrated
  2. custompurified by silica gel chromatography (75 g SG; EtOAc, 20% MeOH/EtOAc)

Sources & evidence

ORD record
ord-01c6b3a09b11483287138172e9fa4b33
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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