Ammonium formate → HCID 178453930, compound

HRID 1257728Notes

Reaction equation

HRID 1257728 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH:14]=[CH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][S:16]([CH3:19])(=[O:17])=[O:18])[CH2:10][CH2:9]1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178453929HCID 178453929, compound

Product 1

HCID 178453930HCID 178453930, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Trans [4-(2-methanesulfonyl-vinyl)-cyclohexyl]-carbamic acid tert-butyl ester (1.00 g, 3.30 mmol) was dissolved in ethanol (15 mL, IMS grade) and 10% palladium on carbon (100 mg) was added, followed by ammonium formate (1.25 g, 19.8 mmol). The mixture was heated at 90° C. for 45 min, then cooled to room temperature. A further 100 mg palladium on carbon was added and the mixture was heated at 95° C. for 16 h. The mixture was cooled to room temperature then filtered and concentrated under vacuum. The residue was taken up in water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine then dried (Na2SO4) and concentrated under vacuum to give 928 mg (92%) of trans [4-(2-methanesulfonyl-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester. LCMS (method Q, ESI): RT=3.35 min, m+H=204.1; NMR (400 MHz, CDCl3) δ: 4.36 (br s, 1H), 3.38 (br s, 1H), 3.01 (m, 2H), 2.89 (s, 3H), 2.07-1.98 (m, 2H), 1.82-1.72 (m, 4H), 1.44 (s, 9H), 1.36-1.08 (m, 5H).

Workup

  1. temperaturecooled to room temperature
  2. temperaturethe mixture was heated at 95° C. for 16 h
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationthen filtered
  5. concentrationconcentrated under vacuum
  6. extractionextracted with ethyl acetate (×3)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialthen dried (Na2SO4)
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-208fd3c8feea4a83a4fb7feb0a95057b
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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