m-Chloroperbenzoic acid → HCID 66763382, compound

HRID 573774Notes

Reaction equation

HRID 573774 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:23])[CH3:22])[C:12]3[C@@H:24]([C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=4)[O:25][C:26]4([CH2:30][CH2:29][CH2:28][CH2:27]4)[C:11]=3[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:49])C=1>C(Cl)(Cl)Cl>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][C:15]2[N+:14]([O-:49])=[C:13]([CH:21]([CH3:23])[CH3:22])[C:12]3[C@@H:24]([C:31]4[CH:32]=[CH:33][C:34]([C:37]([F:38])([F:39])[F:40])=[CH:35][CH:36]=4)[O:25][C:26]4([CH2:30][CH2:29][CH2:28][CH2:27]4)[C:11]=3[C:10]1=2)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66761536HCID 66761536, compound

Product 1

HCID 66763382HCID 66763382, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

280 mg (3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-4′-isopropyl-7′,7′-dimethyl-3′-(4-(trifluoromethyl)phenyl)-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline] are dissolved in 5 ml chloroform and treated with 80 mg of meta-chloroperbenzoic acid (MCPBA) (<77%). The mixture is stirred for 18 hours and then partitioned between dichloromethane and a solution of sodium sulfite in water (5%). The organic phase is washed with saturated aqueous sodium bicarbonate and dried with sodium sulphate. After evaporation of the solvents the residue is chromatographed on silica gel (hexane/ethylacetate 4:1).

Workup

  1. custompartitioned between dichloromethane
  2. washThe organic phase is washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried with sodium sulphate
  4. customAfter evaporation of the solvents the residue
  5. customis chromatographed on silica gel (hexane/ethylacetate 4:1)

Sources & evidence

ORD record
ord-6a8d677fab2d4882a249b3976041ca59
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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