m-Chloroperbenzoic acid → HCID 66811086, compound

HRID 1099182Notes

Reaction equation

HRID 1099182 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-c981c0614288489bb8583d34aa64d8af
Source dataset
uspto-grants-2012_03
Patent number
US08143403B2

Reaction notes

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