Bromocycloheptane → (cis)-4-(3,4-Dimethoxyphenyl)-2-cyclopentyl-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

HRID 1871372Notes

Reaction equation

HRID 1871372 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C@H:20]3[C@H:15]([CH2:16][CH:17]=[CH:18][CH2:19]3)[C:14](=[O:21])[NH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH:22]1(Br)[CH2:28][CH2:27][CH2:26][CH2:25]CC1.COC1C=C(C2[C@H]3[C@H](CCCC3)C(=O)N(C)N=2)C=CC=1OC>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C@H:20]3[C@H:15]([CH2:16][CH:17]=[CH:18][CH2:19]3)[C:14](=[O:21])[N:13]([CH:25]3[CH2:26][CH2:27][CH2:28][CH2:22]3)[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 16992BromocycloheptaneHCID 10935039cis-4-(3,4-Dimethoxyphenyl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-oneHCID 70003942(cis)-4-(3,4-Dimethoxyphenyl)-2-methyl-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one

Product 1

HCID 70002499(cis)-4-(3,4-Dimethoxyphenyl)-2-cyclopentyl-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

Procedure

Prepared from compound 3 and cycloheptylbromide as described for compound 8. Purified by chromatography (dichloromethane) and crystallized from diethyl ether. M.p. 131-133° C.

Workup

  1. customPurified by chromatography (dichloromethane)
  2. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-f879c32621f54060b1907535eb28024b
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

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