Triacetoxyperiodinane → HCID 11988306, compound

HRID 2245245Notes

Reaction equation

HRID 2245245 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][OH:23])[C@@H:18]([CH2:24][NH:25][C:26]3[CH2:30][CH2:29][C:28](=[O:31])[CH:27]=3)[C@@H:17]2[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[F:12][C:9]([F:11])([F:10])[C:7]1[CH:6]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:21][CH2:20][C@H:19]3[C@@H:18]([CH2:24][N:25]([C:26]4[CH2:30][CH2:29][C:28](=[O:31])[CH:27]=4)[CH:22]3[OH:23])[C@@H:17]2[C:32]2[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=2)[CH3:14])[CH:4]=[C:3]([C:2]([F:1])([F:39])[F:40])[CH:8]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 866281103-({[(1R,2R,3S,6S)-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)-6-(hydroxymethyl)cyclohexyl]methyl}amino)cyclopent-2-en-1-one

Product 1

HCID 11988306HCID 11988306, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the intermediate from Step O (20 mg, 0.0348 mmol) in 5 mL dichloromethane was added Dess-Martin periodinane (16 mg, 0.038 mmol) at room temperature. The mixture was stirred at room temperature for 0.5 hr. The solvent was removed under vacuum and the residue was purified by preparative TLC (9.5:5 dichloromethane: 2N NH3 in methanol) to give 8 mg of the title compound. 1H-NMR (CDCl3) δ: 7.71 (1H, s), 7.22 (2H, s), 7.03 (2H, m), 6.90 (2H, m), 5.30, 5.20 (1H, two doublets), 5.28 (1H, two singlets), 4.45 (1H, m), 3.35 (1H, m), 3.20 (1H, m), 3.00 (1H, m), 2.84 (1H, m), 2.55-2.30 (6H, m), 2.03 (1H, m), 1.80-1.85 (4H, m), 1.33 (3H, d, J=6.5 Hz). MS: (MH)+ 572.5.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by preparative TLC (9.5:5 dichloromethane: 2N NH3 in methanol)

Sources & evidence

ORD record
ord-98993dcbd1174aec97096bcc90fef9ce
Source dataset
uspto-grants-2010_03
Patent number
US07683068B2

Reaction notes

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