Water → methyl 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-tert-butoxycarbonylpiperazine-2-carboxylate

HRID 358770Notes

Reaction equation

HRID 358770 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13](Cl)=[O:14])=[CH:8][C:7]=2[CH:16]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][NH:29][CH:28]([C:32]([O-:34])=[O:33])[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].[CH2:35](N(CC)CC)C.O>ClCCl>[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13]([N:29]3[CH2:30][CH2:31][N:26]([C:24]([O:23][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:25])[CH2:27][CH:28]3[C:32]([O:34][CH3:35])=[O:33])=[O:14])=[CH:8][C:7]=2[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10264946HCID 10264946, compoundHCID 225929391,3-Piperazinedicarboxylic acid, 1-(1,1-dimethylethyl) ester

Product 1

HCID 20066655methyl 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-tert-butoxycarbonylpiperazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,3-dimethoxy-6,7-dihydro-5H-benzocycloheptene-8-carbonyl chloride (1.6 g) in dichloromethane (15 ml) is added dropwise, at 0° C. taking 3 minutes, to a mixture of 4-tert-butoxycarbonylpiperazine-2-carboxylate (1.8 g) obtained in Reference Example 16, triethylamine (1.3 g) and dichloromethane (20 ml). The reaction mixture is poured into water and extracted with dichloromethane. The organic layer is washed with water and dried, then the solvent is distilled off under reduced pressure. The residue is purified by means of a silica gel column chromatography (hexane:ethyl acetate:acetone=5:4:1) to afford methyl 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-tert-butoxycarbonylpiperazine-2-carboxylate as a colorless oily product (2.8 g).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer is washed with water
  3. customdried
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe residue is purified by means of a silica gel column chromatography (hexane:ethyl acetate:acetone=5:4:1)

Sources & evidence

ORD record
ord-93af9458b13747c092572329087f930c
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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