HCID 178453883, compound → HCID 178453884, compound

HRID 711960Notes

Reaction equation

HRID 711960 reaction equation
[C:1]([CH:3]=[CH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7][CH2:6]1)#[N:2]>[Pd].C(O)C>[C:1]([CH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH2:7][CH2:6]1)#[N:2]

Participants

4

Reactant 1

HCID 178453883HCID 178453883, compound

Product 1

HCID 178453884HCID 178453884, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl {trans-4-[2-cyanovinyl]cyclohexyl}carbamate (0.13 g, 0.52 mmol) and 10% palladium on carbon (52 mg) in ethanol (2 mL) was hydrogenated under balloon pressure of H2 over weekend. The mixture was filtered, and the filtrate was concentrated to give tert-butyl [trans-4-(2-Cyanoethyl)cyclohexyl]carbamate. LCMS calculated for C10H17N2O2 (M-tBu+H)+: m/z=197.1. Found: 197.1. This carbamate intermediate was treated with trifluoroacetic acid (0.4 mL, 5 mmol) in methylene chloride (1 mL) at room temperature for 1 h, and then the solvent removed to give the desired product as TFA salt. LCMS calculated for C9H17N2 (M+H)+: m/z=153.1. Found: 153.2.

Workup

  1. waitwas hydrogenated under balloon pressure of H2 over weekend
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-151b0213679c423e9df7f72a11941180
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…