HCID 67322581, compound → 4-(Methanesulfonylmethyl)cyclohexan-1-amine

HRID 1257720Notes

Reaction equation

HRID 1257720 reaction equation
C(OC(=O)[NH:10][CH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:13][CH2:12]1)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:21][S:18]([CH2:17][CH:14]1[CH2:15][CH2:16][CH:11]([NH2:10])[CH2:12][CH2:13]1)(=[O:19])=[O:20]

Participants

4

Reactant 1

HCID 67322581HCID 67322581, compound

Product 1

HCID 583459044-(Methanesulfonylmethyl)cyclohexan-1-amineYield 100.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(4-Methanesulfonylmethyl-cyclohexyl)-carbamic acid benzyl ester (0.54 g, 1.66 mmol) in ethanol (15 mL, IMS grade) under nitrogen was treated with 10% palladium/carbon (0.18 g, 0.17 mmol). The mixture was purged with hydrogen gas and was stirred under an atmosphere of hydrogen (balloon) for 16 hours. The catalyst was filtered off through Celite® and the filter cake rinsed several times with ethanol. The filtrate was concentrated and then purified by column chromatography on Isolute® SCX-2 cartridge (eluting with MeOH then 2M NH3 in MeOH). The relevant fractions were combined concentrated under vacuum to afford 0.32 g (95%) 4-methanesulfonylmethyl-cyclohexylamine as clear oil that was used without further purification. LCMS (Method I, ESI): RT=0.35 min, m+H=191.9.

Workup

  1. customThe mixture was purged with hydrogen gas
  2. filtrationThe catalyst was filtered off through Celite®
  3. washthe filter cake rinsed several times with ethanol
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography on Isolute® SCX-2 cartridge (
  6. washeluting with MeOH
  7. concentrationThe relevant fractions were combined concentrated under vacuum

Sources & evidence

ORD record
ord-5a2a656e3a6c4d46b6f1d5efcd3446bc
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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