Trimethylsilyldiazomethane → 4-(4-Chloro-2-methoxycarbonyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 457166Notes

Reaction equation

HRID 457166 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[C:21]([OH:23])=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[C:21]([O:23][CH3:24])=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 665995652-(4-(tert-Butoxycarbonyl)piperazin-1-yl)-5-chlorobenzoic acid

Product 1

HCID 667586124-(4-Chloro-2-methoxycarbonyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

To a solution of 4-(2-Carboxy-4-chloro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.64 g, 1.88 mmol) in toluene: methanol (9:1) was added a trimethylsilyldiazomethane (2.0 M in hexanes) (1.05 mL, 2.07 mmol) and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo and purified using gradient elution from hexane/ethyl acetate (10%) to hexane/ethyl acetate (50%). 1H-NMR (CDCL3) δ: 1.45 (9H, s), 2.90–3.00 (4H, m), 3.50–3.60 (4H, m), 3.90 (3H, s), 6.90–7.00 (1H, d), 7.35–7.45 (1H, dd), 7.80 (1H, d). ESI-MS m/z: 355 (M+1), UV retention time: 3.11 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified
  3. washelution from hexane/ethyl acetate (10%) to hexane/ethyl acetate (50%)

Sources & evidence

ORD record
ord-218ad698391e4b1ea24f15b55f924a0e
Source dataset
uspto-grants-2007_03
Patent number
US07186729B2

Reaction notes

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