Hydrochloric Acid → (2SR,9aRS)-9a-butyl-2,4-dimethyl-7-hydroxy-2-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7861Notes

Reaction equation

[CH2:1]([C:5]12[CH2:17][C:16]([CH3:21])([CH2:18][CH2:19][CH3:20])[C:15](=[O:22])[C:14]([CH3:23])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:24]COC)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].Cl>CO>[CH2:1]([C:5]12[CH2:17][C:16]([CH3:21])([CH2:18][CH2:19][CH3:20])[C:15](=[O:22])[C:14]([CH3:23])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([OH:24])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of (2SR,9aRS)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-2-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (40 mg, 0.11 mmol) in methanol (approx. 0.5-1 mL) was placed under a nitrogen atmosphere and treated with 2N aqueous HCl (0.165 mL, 0.37 mmol). The resulting yellow solution was stirred and heated in an oil bath at 85° C. for 60 minutes. On cooling, the mixture deposited white crystals. The mixture was cooled in an ice bath and filtered. The crystalline product was washed with ice-cold 5:1 MeOH-2N HCl (2×2 mL) and dried under vacuum to afford (2SR,9aRS)-9a-butyl-2,4-dimethyl-7-hydroxy-2-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one.

Workup

temperatureOn cooling
temperatureThe mixture was cooled in an ice bath
filtrationfiltered
washThe crystalline product was washed with ice-cold 5:1 MeOH-2N HCl (2×2 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-58e5100c1cca454d952bc1df3a46b49a
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087599B2

Reaction notes

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