HCID 57565075, compound → HCID 57565073, compound

HRID 1726867Notes

Reaction equation

HRID 1726867 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][O:7][CH2:8][C:9]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH2:13][CH:12]([OH:16])[CH2:11][CH2:10]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]([F:30])([F:31])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][O:7][CH2:8][C:9]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 57565075HCID 57565075, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 57565073HCID 57565073, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylcycloheptanol (26 mg, step F) in dichloromethane (0.5 mL) at room temperature were added pyridinium chlorochromate (25 mg) and powdered 4A° molecular sieves (26 mg), and the resulting mixture was stirred at room temperature for 1.5 h and then filtered through a small pad of silica gel. The filtrate was evaporated in vacuo and the residue was purified by preparative TLC eluting with 30% ethyl acetate/70% hexanes to give the title compound as an oily material (21 mg). 1H NMR (400 MHz, CDCl3) δ 1.74 (3H, m), 1.98 (1H, dd, J=11.6, 1.2 Hz), 2.48 (6H, m), 3.37 (1H, d, J=8.8 Hz), 3.39 (1H, d, J=8.8 Hz), 4.42 (2H, s), 7.28 (1H, m), 7.35 (4H, m), 7.56 (2H, m), and 7.74 (1H, s). HRMS m/z calcd. for C23H21F6O2 (M−H)− 443.1446, found 443.1457.

Workup

  1. filtrationfiltered through a small pad of silica gel
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was purified by preparative TLC
  4. washeluting with 30% ethyl acetate/70% hexanes

Sources & evidence

ORD record
ord-7cb76d2d23ea4a14b19d630843f719c8
Source dataset
uspto-grants-2009_02
Patent number
US07494986B2

Reaction notes

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