Trifluoroacetic acid → HCID 178511086, compound

HRID 1257709Notes

Reaction equation

HRID 1257709 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][C:15]#[N:16])[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][C:15]#[N:16])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178453919HCID 178453919, compound

Product 1

HCID 178511086HCID 178511086, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of trans (4-cyanomethyl-cyclohexyl)-carbamic acid tert-butyl ester (0.71 g, 3.00 mmol) in DCM (15 mL) was treated with trifluoroacetic acid (2 mL) and the mixture was stirred at ambient temperature for 2.5 hours, then concentrated under vacuum. The residue was purified by column chromatography using Isolute SCX-2 cartridge (eluting with MeOH then 2M NH3 in MeOH). The relevant fractions were combined and concentrated under vacuum to afford 0.40 g (97%) of trans (4-amino-cyclohexyl)-acetonitrile that was used without further purification. 1H NMR (400 MHz, CDCl3) δ: 3.52-3.42 (m, 2H), 2.69-2.60 (m, 1H), 2.26 (d, 2H), 1.94-1.83 (m, 4H), 1.70-1.57 (m, 1H), 1.24-1.06 (m, 4H).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by column chromatography
  3. washeluting with MeOH
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6ae9664bca2d4703b72c10abac8301b4
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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