(-)-2-Butanol → (+/-)-(3SR,3aRS)-((R)-sec-butyl) 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate

HRID 505759

Reaction equation

HRID 505759 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:18]([CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:17]3[C:12]([C:13]4[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][C:14]=4[CH2:15][CH2:16]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH3:31][C@@H:32](O)[CH2:33][CH3:34]>>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:18]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[CH:17]3[C:12]([C:13]4[CH:27]=[CH:26][C:25]([C:28]([O:30][C@@H:32]([CH2:33][CH3:34])[CH3:31])=[O:29])=[CH:24][C:14]=4[CH2:15][CH2:16]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

3

Reactant 2

HCID 84682(-)-2-ButanolHCID 24983760(+/-)(3SR,3aRS)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid

Product 1

HCID 68800247(+/-)-(3SR,3aRS)-((R)-sec-butyl) 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylateYield 68%

Procedure

The title compound was prepared from (±)-(3SR,3aRS)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid, Example 15 and (R)-butan-2-ol according to Method E (yellow solid, 155 mg, 0.326 mmol, 68% yield). ES-HRMS m/z calc. for C28H31ClN3O2 (M+H) 476.2099, found 476.2100.

Sources & evidence

ORD record
ord-1804d183a7df4d24968994cfede87a89
Source dataset
uspto-grants-2010_08
Patent number
US07781428B2

Linked notes

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