Tributylphosphine → HCID 66941040, compound

HRID 1864080Notes

Reaction equation

HRID 1864080 reaction equation
O[CH2:2][C@H:3]([NH:5][CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)=[O:8])[CH3:4].C(P(CCCC)CCCC)CCC>CCOC(C)=O>[CH3:2][C@@H:3]1[CH2:4][N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[C:7](=[O:8])[CH2:6][NH:5]1

Participants

4

Reactant 2

HCID 13831TributylphosphineHCID 66940887HCID 66940887, compound

Product 1

HCID 66941040HCID 66941040, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of N2-[(1R)-2-hydroxy-1-methylethyl]-N1-(3-nitrophenyl)glycinamide (2.0 g, 7.9 mmol) and tributylphosphine (2.7 mL, 15.8 mmol) in EtOAc (21 mL) was slowly added a solution of di-t-butylazodicarboxlate, (3.6 g, 15.8 mmol) in EtOAc 10 mL. The inside temperature was kept between 25° C. to 30° C. The reaction was followed by HPLC. The crude material was purified a silica gel column chromatography (2% to 5% MeOH in CH2Cl2). The compound (5R)-5-methyl-1-(3-nitrophenyl)-2-piperazinone was isolated as solid (690 mg, 37% yield) MS: M(C11H13N3O3)=235.24 (M+H)+=236.

Workup

  1. customwas kept between 25° C. to 30° C
  2. customThe crude material was purified a silica gel column chromatography (2% to 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-019d853025f749a88989f289ca393171
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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