Trifluoroacetic acid → Trifluoroacetic acid

HRID 711961Notes

Reaction equation

HRID 711961 reaction equation
[C:1]([CH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11]C(=O)OC(C)(C)C)[CH2:7][CH2:6]1)#[N:2].[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22]>C(Cl)Cl>[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22].[NH2:11][C@H:8]1[CH2:9][CH2:10][C@H:5]([CH2:4][CH2:3][C:1]#[N:2])[CH2:6][CH2:7]1.[C:21]([OH:23])([C:20]([F:25])([F:24])[F:19])=[O:22]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178453884HCID 178453884, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 178511030HCID 178511030, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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. customthe solvent removed

Sources & evidence

ORD record
ord-49bedd98e92645b09991bd094b92b006
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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