Heptyl-[2-(4-hydroxymethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester → [2-(4-Formyl-phenyl)-ethyl]-heptyl-carbamic acid tert-butyl ester

HRID 47790Notes

Reaction equation

HRID 47790 reaction equation
[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]>CCOCC.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 69883655Heptyl-[2-(4-hydroxymethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 86586368[2-(4-Formyl-phenyl)-ethyl]-heptyl-carbamic acid tert-butyl esterYield 76.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of heptyl-[2-(4-hydroxymethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester (4.9 mmol, 1.7 g) in anhydrous ether (50 mL) was added activated manganese dioxide (Aldrich, 5 g). The resulting suspension was stirred at room temperature adding further 2 g portions of manganese dioxide every 2 hours until the starting material had been consumed as determined by TLC. The mixture was filtered through a Celite® plug and washed through exhaustively with dichloromethane. The yellow filtrate was concentrated to a yellow oil which was chromatographed on silica gel (20% ethyl acetate/hexanes) to give [2-(4-formyl-phenyl)-ethyl]-heptyl-carbamic acid tert-butyl ester as a clear oil (1.30 g, 76%).

Workup

  1. customhad been consumed
  2. filtrationThe mixture was filtered through a Celite® plug
  3. washwashed through exhaustively with dichloromethane
  4. concentrationThe yellow filtrate was concentrated to a yellow oil which
  5. customwas chromatographed on silica gel (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-28dd524290f4471ea623c6c82934819a
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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