Triphenylphosphine → ((R)-1-benzenesulfonyl-aziridin-2-yl)-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-methanone

HRID 1864366Notes

Reaction equation

HRID 1864366 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:29])[CH:16]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:17]O)[CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:23]1([S:20]([N:19]2[CH2:17][CH:16]2[C:15]([N:12]2[CH2:11][CH2:10][N:9]([C:3]3[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=3[CH3:1])[CH2:14][CH2:13]2)=[O:29])(=[O:22])=[O:21])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 67141139HCID 67141139, compound

Product 1

HCID 86623480((R)-1-benzenesulfonyl-aziridin-2-yl)-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-methanoneYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (RS)—N-{2-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-1-hydroxymethyl-2-oxo-ethyl}-benzenesulfonamide (1.417 g) and triphenylphosphine (0.979 g) in tetrahydrofuran (12 ml) was added diethylazodicarboxylate (DEAD, 0.65 g) at 0° C. After 15 min the ice bath was removed and the mixture was stirred at room temperature for 45 min. The solvent was evaporated and the product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 4:1=>1:1) to give (RS)-(1-benzenesulfonyl-aziridin-2-yl)-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-methanone (0.934 g) as a colorless solid.

Workup

  1. customAfter 15 min the ice bath was removed
  2. customThe solvent was evaporated
  3. customthe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 4:1=>1:1)

Sources & evidence

ORD record
ord-712d7c403b114d3fa23b4e20261049a1
Source dataset
uspto-grants-2009_12
Patent number
US07625902B2

Reaction notes

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