Hydrochloric Acid → HCID 178484035, compound

HRID 967142Notes

Reaction equation

HRID 967142 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[N:10]([CH3:21])[CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18][CH:19]=[O:20])[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO>[CH2:1]([O:8][C:9](=[O:22])[N:10]([CH2:11][C@H:12]1[CH2:13][CH2:14][C@H:15]([CH2:18][CH2:19][OH:20])[CH2:16][CH2:17]1)[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 178484034HCID 178484034, compound

Product 1

HCID 178484035HCID 178484035, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 0.75 g (2.47 mmol) trans-methyl-[4-(2-oxo-ethyl)-cyclohexylmethyl]-carbamic acid benzyl ester in 15 ml of methanol was cooled to 0-5° C. 0.14 g (3.7 mmol) of sodium borohydride were added in four equal portions, at intervals of 10 minutes. Stirring was continued for 1 hour at room temperature. Afterwards, a 1N aqueous hydrochloric acid solution was dropped into the solution until the medium was acidic; it was then made neutral by addition of aqueous sodium bicarbonate solution. The reaction mixture was subsequently extracted 3 times with 25 ml of dichloromethane. The combined organic phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue obtained was chromatographed on silica gel with a 95:5 v/v mixture of dichloromethane and methanol as the eluent. 0.63 g (83%) trans-[4-(2-hydroxy-ethyl)-cyclohexylmethyl]-methyl-carbamic acid benzyl ester were obtained as colorless oil, MS: 306 (MH+).

Workup

  1. extractionThe reaction mixture was subsequently extracted 3 times with 25 ml of dichloromethane
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue obtained
  5. customwas chromatographed on silica gel with a 95:5 v/v mixture of dichloromethane and methanol as the eluent

Sources & evidence

ORD record
ord-397b344607dd4c90ac86fb93a4e7bb43
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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