p-Toluenesulfonic acid → HCID 131730843, compound

HRID 42533Notes

Reaction equation

HRID 42533 reaction equation
C1([C@H]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])C)C=CC=CC=1.[S:21]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)([OH:24])(=[O:23])=[O:22]>C(O)C.[Pd]>[S:21]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)([OH:24])(=[O:23])=[O:22].[NH2:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15252753HCID 15252753, compound

Product 1

HCID 131730843HCID 131730843, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent3×

Procedure

10% Pd/C (Degussa, 50% wet, 0.87 g) was carefully wetted down under argon with ethanol, then (1S,2R)-ethyl 2-((R)-1-phenylethylamino)cyclohexane-carboxylate, tosylic acid (8.7 g, 19.4 mmol) in ethanol (75 mL) was added. The mixture was then hydrogenated for 20 hours at 50 psi in a Parr shaker apparatus. Under argon, the catalyst was filtered off. The filtrate was resubjected to hydrogenation, this time with 1.70 grams of 10% Pd/C (Degussa, 50% wet). After 6 hours, the reaction was analyzed by LCMS, which detected little change. Under argon, the reaction was carefully filtered through a fiberglass filter paper. The filtrate was concentrated to give a colorless oil. The oil was resubjected to 10% Pd/C (Degussa, 50% wet, 1.70 grams) in 50 mL of ethanol and hydrogenated for 20 hours at 50 psi. Under argon, the reaction was carefully filtered through a fiberglass filter paper. The filtrate was concentrated to give (1S,2R)-ethyl 2-aminocyclohexanecarboxylate tosylic acid (5.4 g, 15.7 mmol, 81% yield) as a colorless oil. MS (ESI+)=172.16 (M+H)+.

Workup

  1. filtrationUnder argon, the catalyst was filtered off
  2. waitAfter 6 hours
  3. filtrationUnder argon, the reaction was carefully filtered through a fiberglass
  4. filtrationfilter paper
  5. concentrationThe filtrate was concentrated
  6. customto give a colorless oil
  7. waithydrogenated for 20 hours at 50 psi
  8. filtrationUnder argon, the reaction was carefully filtered through a fiberglass
  9. filtrationfilter paper
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6b8d5fd7e6a3450ea1c6941a163377e7
Source dataset
uspto-grants-2013_09
Patent number
US08536198B2

Reaction notes

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