Heptyl-[1-(4-hydroxymethyl-phenyl)-cyclopropylmethyl]-carbamic acid tert-butyl ester → [1-(4-Formyl-phenyl)-cyclopropylmethyl]-heptyl-carbamic acid tert-butyl ester

HRID 47806Notes

Reaction equation

HRID 47806 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:8][C:9]1([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][CH:13]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]>C(OCC)C.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:8][C:9]1([C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][CH:13]=2)[CH2:11][CH2:10]1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 69884085Heptyl-[1-(4-hydroxymethyl-phenyl)-cyclopropylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 86586369[1-(4-Formyl-phenyl)-cyclopropylmethyl]-heptyl-carbamic acid tert-butyl esterYield 77%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of heptyl-[1-(4-hydroxymethyl-phenyl)-cyclopropylmethyl]-carbamic acid tert-butyl ester (850 mg, 2.24 mmol) in anhydrous diethyl ether (25 mL) under an nitrogen atmosphere was added activated manganese dioxide (Aldrich, 2.25 g). The solution was allowed to stir at room temperature for 2 hours. An additional 1 g of manganese dioxide was added and the mixture was stirred for 2 hours. The heterogeneous black mixture was filtered through a Celite plug and was washed exhaustively with methylene chloride. The clear filtrate was concentrated to a crude yellow tinged oil. The crude mixture was purified by flash chromatography (15% ethyl acetate/hexanes) to give [1-(4-formyl-phenyl)-cyclopropylmethyl]-heptyl-carbamic acid tert-butyl ester as a clear oil (640 mg, 77%).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. filtrationThe heterogeneous black mixture was filtered through a Celite plug
  3. washwas washed exhaustively with methylene chloride
  4. concentrationThe clear filtrate was concentrated to a crude yellow tinged oil
  5. customThe crude mixture was purified by flash chromatography (15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6ecf42d1ecc34d81b5af70191b9e3450
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

Loading…