Acetic Acid → HCID 18417041, compound

HRID 990917Notes

Reaction equation

HRID 990917 reaction equation
C(OC(=O)[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17](=[O:25])[NH:18][CH:19]([C:23]#[N:24])[CH:20]1[CH2:22][CH2:21]1)C1C=CC=CC=1.[CH3:27][C:28]([OH:30])=[O:29].C1CCCCC1>CCOC(C)=O.[Pd]>[C:28]([OH:30])(=[O:29])[CH3:27].[C:23]([CH:19]([NH:18][C:17]([CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[NH2:10])=[O:25])[CH:20]1[CH2:21][CH2:22]1)#[N:24]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8078CyclohexaneHCID 69760119HCID 69760119, compound

Product 1

HCID 18417041HCID 18417041, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[(1-cyano-1-cyclopropyl-methyl)-carbamoyl]-cyclohexyl-carbamic acid benzyl ester (0.15 g, 0.42 mmol) in 50 ml EtOAc with 1% HOAc (v/v) is added Pd/C (10%) (0.05 g) carefully under nitrogen. The mixture is degassed completely before the reaction flask is filled with H2 through a balloon. The reaction mixture is stirred for 45 minutes. TLC showed that the starting material has disappeared. The reaction mixture is filtered through Celite. The filtrate is concentrated to give a yellow oil. Yield: 0.17 g, 100%. The isolated cis- and trans-forms of the product are obtained by starting from the corresponding cis- or trans-form of the cyclohexane derivative.

Workup

  1. customThe mixture is degassed completely before the reaction flask
  2. additionis filled with H2 through a balloon
  3. filtrationThe reaction mixture is filtered through Celite
  4. concentrationThe filtrate is concentrated
  5. customto give a yellow oil
  6. customThe isolated cis- and trans-forms of the product are obtained

Sources & evidence

ORD record
ord-807c90a313b0470a93a79c8146a80023
Source dataset
uspto-grants-2002_10
Patent number
US06462076B2

Reaction notes

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