HCID 68765812, compound → HCID 86609417, compound

HRID 1171649Notes

Reaction equation

HRID 1171649 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11]/[C:10]/1=[CH:34]\[CH2:35][OH:36])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:11]/[C:10]/1=[CH:34]\[CH:35]=[O:36])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 68765812HCID 68765812, compound

Product 1

HCID 86609417HCID 86609417, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-4-(t-butyldimethylsilyloxy)-3-(2-hydroxyethylidene)-1-(triphenylmethyl)piperidine (8.50 g) in dichloromethane (120 ml) was added manganese dioxide (8.87 g) at room temperature, and the resulting mixture was stirred at room temperature for 45 hours. After stirring, the insoluble materials were filtered off. The filtrate was evaporated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (3:17) as the eluent to afford the title compound (7.54 g, yield: 89%) as a colourless amorphous solid.

Workup

  1. stirringAfter stirring
  2. filtrationthe insoluble materials were filtered off
  3. customThe filtrate was evaporated in vacuo
  4. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2541f7090e3b4891995329117406285d
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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