Potassium bisulfate → HCID 178486044, compound

HRID 25577Notes

Reaction equation

HRID 25577 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12](=[O:27])[N:13]([C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21](=[O:26])N(OC)C)[CH2:17][CH2:16]1)[CH3:14])([CH3:10])([CH3:9])[CH3:8].OS([O-])(=O)=O.[K+]>C1COCC1>[C:7]([O:11][C:12](=[O:27])[N:13]([C@H:15]1[CH2:16][CH2:17][C@H:18]([CH:21]=[O:26])[CH2:19][CH2:20]1)[CH3:14])([CH3:8])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 178502727HCID 178502727, compound

Product 1

HCID 178486044HCID 178486044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 2.09 g (55 mmol) LAH in 250 ml THF was cooled (−50° C.) and treated during 25 min with a solution of 15.02 g (50 mmol) of trans-[4-(Methoxy-methyl-carbamoyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 250 ml THF. The reaction was warmed up to +15° C. for 3.5 h, cooled (−78° C.) and hydrolyzed with a suspension of 15 g MgSO4.7H2O, 15 g silicagel in 50 ml aqueous 10% KHSO4. The cooling bath was removed, THF was added, the mixture was stirred for 30 min and filtered. After evaporation, the residue was dissolved in CH2Cl2, dried over Na2SO4 and evaporated to yield 12.83 (quantitative) trans-(4-Formyl-cyclohexyl)-methyl-carbamic acid tert-butyl ester, MS: 241 (M).

Workup

  1. temperatureThe reaction was warmed up to +15° C. for 3.5 h
  2. customThe cooling bath was removed
  3. additionTHF was added
  4. filtrationfiltered
  5. customAfter evaporation
  6. dissolutionthe residue was dissolved in CH2Cl2
  7. dry with materialdried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-6022171bfbfc41a88f67c0c30a82e5ba
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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