Ethanol → trans-4-Hydroxy-5-phenyl-2,3,4,5-tetrahydo spiro(benzothiepine-3,1'-cyclohexane)-1,1-dioxide

HRID 1837651Notes

Reaction equation

HRID 1837651 reaction equation
[C:1]1([C:7]23[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[S:17](=[O:25])(=[O:24])[CH2:16][C:10]4([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]4)[CH:8]2[O:9]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[H][H]>[Pd].C(Cl)Cl>[OH:9][C@@H:8]1[C:10]2([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:16][S:17](=[O:25])(=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C@H:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 223252128b-Phenyl-1a,2,3,8b-tetrahydrospiro(benzothiepino[4,5-b]oxirene-2,1'-cyclohexane)-4,4-dioxideHCID 178418361HCID 178418361, compound

Product 1

HCID 59890377trans-4-Hydroxy-5-phenyl-2,3,4,5-tetrahydo spiro(benzothiepine-3,1'-cyclohexane)-1,1-dioxideYield 40.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.5 g (1.4 mmoles) of 58, 20 ml of ethanol, 10 ml of methylene chloride and 0.4 g of 10% Pd/C catalyst was hydrogenated with 70 psi hydrogen for 3 h at room temperature. The crude reaction slurry was filtered through Celite and evaporated to dryness. The residue was purified by HPLC (10% EtOAc-Hexane, 25% EtOAc-Hexane). The first fraction was 300 mg (60%) as a white solid, mp 99-100° C. Proton NMR showed this was a trans isomer. The second fraction gave 200 mg of solid which was impure cis isomer.

Workup

  1. customThe crude reaction slurry
  2. filtrationwas filtered through Celite
  3. customevaporated to dryness
  4. customThe residue was purified by HPLC (10% EtOAc-Hexane, 25% EtOAc-Hexane)

Sources & evidence

ORD record
ord-b2c974fdcaf7415bb1b394f60e4cd841
Source dataset
uspto-grants-2004_08
Patent number
US06784201B2

Reaction notes

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