Hydrochloric Acid → HCID 178486042, compound

HRID 25591Notes

Reaction equation

HRID 25591 reaction equation
C([O:3][C:4](=O)[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)C.[Li+].[BH4-].Cl>C1COCC1>[C:18]([O:17][C:15](=[O:16])[N:13]([C@H:10]1[CH2:9][CH2:8][C@H:7]([CH2:6][CH2:5][CH2:4][OH:3])[CH2:12][CH2:11]1)[CH3:14])([CH3:19])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 178471546HCID 178471546, compound

Product 1

HCID 178486042HCID 178486042, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

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. temperatureThe solution was refluxed for 8 h
  2. customto destroy excess of LiBH4
  3. additionThe reaction-mixture was diluted with Et2O
  4. washwashed with water
  5. customThe organic layers were evaporated to dryness

Sources & evidence

ORD record
ord-5b4ca01325a541cfb064a354791af53a
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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