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

HRID 358770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358770
[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

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 102649462,3-dimethoxy-6,7-dihydro-5H-benzocycloheptene-8-carbonylchlorideHCID 225929391,3-Piperazinedicarboxylic acid, 1-(1,1-dimethylethyl) ester

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-93af9458b13747c092572329087f930c
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997836

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