Sodium Bisulfate → HCID 178455813, compound

HRID 1801446Notes

Reaction equation

HRID 1801446 reaction equation
[C:1](O[K])(C)(C)C.[C:7]([O:11][C:12](=[O:22])[NH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([CH:20]=O)[CH2:16][CH2:15]1)([CH3:10])([CH3:9])[CH3:8].OS([O-])(=O)=O.[Na+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CC(=O)OCC>[C:7]([O:11][C:12](=[O:22])[NH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([CH:20]=[CH2:1])[CH2:16][CH2:15]1)([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 3

HCID 516919Sodium BisulfateHCID 178418922HCID 178418922, compoundHCID 178453955HCID 178453955, compound

Product 1

HCID 178455813HCID 178455813, compoundYield 98.2%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

tBuOK (13.78 g, 122.7 mmol) was added in one portion to a white suspension of methyl triphenylphosphonium bromide (43.85 g, 122.7 mmol) in THF (145 mL) at rt under nitrogen. The resulting suspension was stirred for 1 h at rt and a solution of trans-(4-formyl-cyclohexyl)-carbamic acid tert-butyl ester (13.95 g, 61.37 mmol) in THF (40 mL) was added. The mixture was stirred 30 min at rt. A 10% NaHSO4 solution (240 mL) was added and the mixture was diluted with EA (500 mL). The two layers were decanted and the aq. layer was extracted once with EA (250 mL). The combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was quickly filtered (EA-Hept 1-2) to afford the title compound as a white solid (13.58 g).

Workup

  1. stirringThe mixture was stirred 30 min at rt
  2. customThe two layers were decanted
  3. extractionthe aq. layer was extracted once with EA (250 mL)
  4. washlayers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. filtrationThe residue was quickly filtered (EA-Hept 1-2)

Sources & evidence

ORD record
ord-1418fba3b36c4a918148621a776e9182
Source dataset
uspto-grants-2013_01
Patent number
US08349829B2

Reaction notes

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