HCID 178471545, compound → HCID 178471546, compound

HRID 25590Notes

Reaction equation

HRID 25590 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH:5]=[CH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:14])[CH2:9][CH2:8]1)[CH3:2]>[Pd]>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:14])[CH2:9][CH2:8]1)[CH3:2]

Participants

3

Reactant 1

HCID 178471545HCID 178471545, compound

Product 1

HCID 178471546HCID 178471546, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 6 g (19.26 mmol) trans-3-[4-(tert-Butoxy carbonyl methyl-amino)-cyclohexyl]-acrylic acid ethyl-ester and 600 mg of Pd/C (10%) was stirred over H2-atmosphere for 20 h. After filtration of the solution, the methanol was evaporated under reduced pressure to yield 5.82 g of clean trans-3-[4-(tert-Butoxycarbonyl methyl-amino)cyclohexyl]-propanoic acid ethyl-ester. To a solution of this ester in 60 ml of THF was added 917 mg (40 mmol) LiBH4. The solution was refluxed for 8 h and then cooled with an ice-bath to 0° C. At this temperature was dropped slowly 1N HCl to the reaction-mixture to destroy excess of LiBH4. The reaction-mixture was diluted with Et2O and then washed with water. The organic layers were evaporated to dryness to yield 3.39 g (73%) of clean trans-[4-(3-Hydroxy-propyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester, MS: 271 (M).

Workup

  1. filtrationAfter filtration of the solution
  2. customthe methanol was evaporated under reduced pressure

Sources & evidence

ORD record
ord-365252dcc71a482187b3ae36d69571eb
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

Loading…