m-Chloroperbenzoic acid → HCID 66811086, compound

HRID 1666149Notes

Reaction equation

HRID 1666149 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F:12][C:13]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=1[C@@H:20]1[CH2:30][CH2:29][C@@H:28]([O:31][Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH2:21]1>C(Cl)Cl>[F:12][C:13]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=1[C@@H:20]1[CH2:30][CH2:29][C@@H:28]([O:31][Si:32]([CH:36]([CH3:38])[CH3:37])([CH:39]([CH3:41])[CH3:40])[CH:33]([CH3:34])[CH3:35])[C:23]2=[N+:24]([O-:9])[CH:25]=[CH:26][CH:27]=[C:22]2[CH2:21]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57911445HCID 57911445, compound

Product 1

HCID 66811086HCID 66811086, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (1.239 g, 5.53 mmol) was added to the CH2Cl2 (30 mL) solution of (6R,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine (2.17 g, 5.03 mmol) at rt. The reaction was stirred at room temperature overnight. The solvent was removed via vacuum. The product was purified by flash column eluted with ethyl acetate in hexane from 0 to 50% to 85%. The product was obtained by flushing the column with 85% ethyl acetate in hexane (1.572 g, 69%). MS(ESI)[M+H+]=448.21; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.14 (br.s., 1H) 6.94-7.11 (m, 2H) 6.84-6.92 (m, 2H) 6.66-6.72 (m, 1H) 6.42 (t, J=4.28 Hz, 1H) 4.04 (dd, J=14.73, 4.41 Hz, 1H) 3.73-3.88 (m, 1H) 2.96 (dd, J=14.48, 5.41 Hz, 1H) 2.50 (d, J=5.79 Hz, 1H) 2.13-2.25 (m, 2H) 1.80-1.94 (m, 1H) 1.18-1.32 (m, 3H) 1.09 (d, J=7.55 Hz, 9H) 1.00 (d, J=7.55 Hz, 9H).

Workup

  1. customThe solvent was removed via vacuum
  2. customThe product was purified by flash column
  3. washeluted with ethyl acetate in hexane from 0 to 50% to 85%
  4. customThe product was obtained
  5. customby flushing the column with 85% ethyl acetate in hexane (1.572 g, 69%)

Sources & evidence

ORD record
ord-d3a0bc55ca604c4f9650d9f6fa7fdd6c
Source dataset
uspto-grants-2011_10
Patent number
US08044043B2

Reaction notes

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