Trifluoroacetic acid → HCID 71279749, compound

HRID 246162Notes

Reaction equation

HRID 246162 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]#[N:15])[CH2:9]1)(C)(C)C.[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20]>ClCCl>[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20].[NH2:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]#[N:15])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71279909HCID 71279909, compound

Product 1

HCID 71279749HCID 71279749, compoundYield 142.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 25 mL round-bottomed flask, cis-(3-cyano-cyclohexyl)-carbamic acid tert-butyl ester (212 mg, 0.945 mmol) was combined with dichloromethane (3 ml) to give a colorless solution. Trifluoroacetic acid (0.9 mL, 11.7 mmol) was added to give a yellow solution which was stirred at room temperature for 1.5 h. The reaction mixture was then concentrated under reduced pressure. The residue was azeotroped with toluene to afford 321 mg of cis-3-aminocyclohexanecarbonitrile trifluoroacetate as a crude solid that was taken to the next step without purification. 1H NMR (300 MHz, DMSO-d6) δ: 7.96 (br. s., 3H), 2.93-3.14 (m, 1H), 2.87 (tt, J=12.2, 3.5 Hz, 1H), 2.22 (d, J=12.1 Hz, 1H), 1.96 (d, J=10.2 Hz, 1H), 1.87 (d, J=11.3 Hz, 1H), 1.68-1.81 (m, 1H), 1.49 (q, J=12.1 Hz, 1H), 1.18-1.41 (m, 3H).

Workup

  1. customto give a colorless solution
  2. customto give a yellow solution which
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. customThe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-82586e0cc5994bbdad5c4661f240ac64
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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