Trimethylsilyldiazomethane → 1-Benzyl 4-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate

HRID 44811

Reaction equation

HRID 44811 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]1[C:24]([OH:26])=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][Si](C=[N+]=[N-])(C)C>CO>[N:11]1([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[CH2:13][CH:12]1[C:24]([O:26][CH3:27])=[O:25]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 2756777N-4-Boc-N-1-Cbz-2-piperazine carboxylic acid

Product 1

HCID 44519651-Benzyl 4-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(Benzyloxycarbonyl)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (1-JJ, 1.07 g, 2.9 mmol, Small Molecules, Inc., Hoboken, N.J. USA) was dissolved in 10 mL of dry methanol and trimethylsilyl diazomethane (2.0 M in diethyl ether, Aldrich) was added dropwise with stirring at rt until a slight yellow color persisted. The solution was then concentrated under reduced pressure, and flash chromatography (0-50% EtOAc/hexanes elution) gave 1-benzyl 4-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate (compound II-JJ) as a colorless oil: [M+Na]+=401.2 (35%); [M-Boc+H]+=279.1 (100%).

Workup

  1. concentrationThe solution was then concentrated under reduced pressure, and flash chromatography (0-50% EtOAc/hexanes elution)

Sources & evidence

ORD record
ord-a8fddb8885d34600a6f07993de8b5f10
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Linked notes

Loading…