HCID 70066577, compound → HCID 70065561, compound

HRID 726675Notes

Reaction equation

HRID 726675 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@@H:15]([C:23]3[CH:28]=[CH:27][C:26]([CH:29]([OH:31])[CH3:30])=[CH:25][CH:24]=3)[CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@@H:15]([C:23]3[CH:24]=[CH:25][C:26]([C:29](=[O:31])[CH3:30])=[CH:27][CH:28]=3)[CH2:16][C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 70066577HCID 70066577, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 70065561HCID 70065561, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (R)-4-{2-(3-cyclopentyloxy-4-methoxyphenyl)-2-[4-(1-hydroxyethyl)-phenyl]ethyl}pyridine from Example 5 (205 mg, 0.49 mmol) in CH2Cl2 (4 mL) was added to a suspension of pyridinium chlorochromate (272 mg, 1.3 mmol) and molecular sieve in CH2Cl2 (3 mL). The reaction mixture was stirred at room temperature for 1 hour before the volatiles were evaporated. The residue was then triturated in EtOAc and filtered over celite. Evaporation of the filtrate afforded a residue which was purified by flash-chromatography (silica gel, hexane/EtOAc 25:75) to afford the title compound as a white foam (39 mg, 19%). 1H NMR (400 MHz, CDCl3): d 1.55 (m, 2H), 175 (m, 6H), 2.55 (s, 3H), 3.30 (d, 2H), 3.80 (s, 3H), 4.20 (t, 1H), 4.65 (m, 1H), 6.60 (s, 1H), 6.65 (d, 1H), 6.75 (d, 1H), 6.90 (d, 2H), 7.25 (d, 2H), 7.85 (d, 2H), 8.40 (d, 2H).

Workup

  1. customwere evaporated
  2. customThe residue was then triturated in EtOAc
  3. filtrationfiltered over celite
  4. customEvaporation of the filtrate
  5. customafforded a residue which
  6. customwas purified by flash-chromatography (silica gel, hexane/EtOAc 25:75)

Sources & evidence

ORD record
ord-f72662ecda3a4fc38363d1fae93e2ee6
Source dataset
uspto-grants-1998_01
Patent number
US05710160

Reaction notes

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