Potassium bisulfate → HCID 178484048, compound

HRID 1743795Notes

Reaction equation

HRID 1743795 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12](=[O:28])[N:13]([CH2:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22](=[O:27])N(OC)C)[CH2:18][CH2:17]1)[CH3:14])([CH3:10])([CH3:9])[CH3:8].OS([O-])(=O)=O.[K+]>C1COCC1>[C:7]([O:11][C:12](=[O:28])[N:13]([CH2:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([CH:22]=[O:27])[CH2:18][CH2:17]1)[CH3:14])([CH3:8])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 178502718HCID 178502718, compound

Product 1

HCID 178484048HCID 178484048, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 12.25 g (313.11 mmol) LAH in 1.3 l THF was cooled (−50° C.) and treated during 30 min with a solution of 89.5 g (284.64 mmol) of trans-[4-(Methoxy-methyl-carbamoyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester in 1.3 l THF. After 20 min at this temperature, the reaction was warmed up to 0° C., cooled (−78° C.) and hydrolyzed with a suspension of 90 g MgSO4.7H2O, 90 g silicagel in 292 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 90.4 (quantitative) of trans-(4-Formyl-cyclohexylmethyl)-methyl-carbamic acid tert-butyl ester, MS: 255 (M).

Workup

  1. temperaturecooled (−78° C.)
  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-ecde24ac7aec4859a1cc8f1159b93779
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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