1,4-Dioxaspiro[4.5]decane, 8-[4-(3,4-difluorophenyl)-3-cyclohexen-1-yl]- → HCID 178505735, compound

HRID 2081522Notes

Reaction equation

HRID 2081522 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:14][CH2:13][CH:12]([CH:15]3[CH2:24][CH2:23][C:18]4([O:22][CH2:21][CH2:20][O:19]4)[CH2:17][CH2:16]3)[CH2:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[H][H]>C(O)C.[Ni]>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:10][CH2:11][C@H:12]([CH:15]3[CH2:24][CH2:23][C:18]4([O:19][CH2:20][CH2:21][O:22]4)[CH2:17][CH2:16]3)[CH2:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 115590611,4-Dioxaspiro[4.5]decane, 8-[4-(3,4-difluorophenyl)-3-cyclohexen-1-yl]-HCID 178418361HCID 178418361, compound

Product 1

HCID 178505735HCID 178505735, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 4.9 g of 8-[4-(3,4-difluorophenyl)-3-cyclohexenyl]-1.4-dioxaspiro[4.5]decane in 670 ml of ethanol was hydrogenated with 1.0 g Raney nickel at 50° C. under normal pressure until the hydrogen uptake came to a standstill. The reaction mixture was filtered and the filtrate was concentrated. Threefold recrystallization of the obtained crude product (5.0 g) from diethyl ether/hexane yielded 2.52 g of 8-[trans-4-(3,4-difluorophenyl)cyclohexyl]-1, 4-dioxaspiro[4.5]decane. The mother liquors were evaporated. Isomerization of the residue (2.2 g) under inert gas with 11 ml of dimethyl sulfoxide and 0.344 g of potassium tert. butylate at 100° C. for 7 hours yielded after twofold recrystallization further 0.7 g of 8-[trans-4-(3,4-difluorophenyl)cyclohexyl]-1,4-dioxaspiro-[4.5]-decane.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThreefold recrystallization of the
  4. customobtained crude product (5.0 g) from diethyl ether/hexane

Sources & evidence

ORD record
ord-b389d3ff904446a1b52531c1660ceb85
Source dataset
uspto-grants-1993_02
Patent number
US05185098

Reaction notes

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