HCID 70849584, compound → HCID 68449340, compound

HRID 2220572Notes

Reaction equation

HRID 2220572 reaction equation
[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][C:7]2[CH:8]3[CH2:14][CH2:13][C:12]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[C:17]([F:24])[C:16]=4[F:25])=[CH:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:28])[CH3:2].C(OC1C=CC2C3CC=C(C4C=CC(OCC)=C(F)C=4F)CC3OC=2C=1F)C>C(OCC)(=O)C.C(O)C.[Ni]>[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][C:7]2[CH:8]3[CH2:14][CH2:13][CH:12]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[C:17]([F:24])[C:16]=4[F:25])[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:28])[CH3:2]

Participants

5

Reactant 2

HCID 70849584HCID 70849584, compoundHCID 72483449HCID 72483449, compound

Product 1

HCID 68449340HCID 68449340, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

7.4 g (about 19.0 mmol) of a mixture of (±)-(4aR*, 9bS*)-7-ethoxy-3-(4-ethoxy-2,3-difluorophenyl)-6-fluoro-1,2,4a,9b-tetrahydrodibenzofuran and (±)-(4aR*, 9bS*)-7-ethoxy-3-(4-ethoxy-2,3-difluorophenyl)-6-fluoro-1,4,4a,9b-tetrahydrodibenzofuran in 160 ml of ethyl acetate/ethanol mixture (3:1) are hydrogenated at 80° C. in the presence of 3.70 g of Raney nickel and 1.50 g of ion exchanger (weakly H-acidic) under hydrogen pressure (4.4 bar). After 18 h, the catalyst is filtered off, and the filtrate is concentrated to dryness. The crude product is recrystallised successively from isopropanol, n-heptane and ethanol, giving (±)-(3R*, 4aR*, 9bS*)-7-ethoxy-3-(4-ethoxy-2,3-difluorophenyl)-6-fluoro-1,2,3,4,4a,9b-hexahydrodibenzofuran as colourless solid (melting point 126° C.).

Workup

  1. filtrationthe catalyst is filtered off
  2. concentrationthe filtrate is concentrated to dryness
  3. customThe crude product is recrystallised successively from isopropanol, n-heptane and ethanol

Sources & evidence

ORD record
ord-9ec64dd8fff9473582994d91d7405921
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

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