Trifluoroacetic acid → HCID 178511418, compound

HRID 1257703Notes

Reaction equation

HRID 1257703 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([O:14][CH2:15][C:16]#[N:17])[CH2:10][CH2:9]1)(C)(C)C.[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22]>C(Cl)Cl.C1(C)C=CC=CC=1>[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22].[NH2:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([O:14][CH2:15][C:16]#[N:17])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454073HCID 178454073, compound

Product 1

HCID 178511418HCID 178511418, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of trans (4-cyanomethoxy-cyclohexyl)-carbamic acid tert-butyl ester (280 mg, 1.10 mmol) in DCM (22 mL) was treated with trifluoroacetic acid (22 mL) and stirred at ambient temperature for 30 minutes. The mixture was diluted with toluene and concentrated under vacuum. The residue was azeotroped with toluene to afford 450 mg (quantitative yield) of trans (4-amino-cyclohexyloxy)-acetonitrile trifluoroacetic acid salt as a colourless oil. LCMS (Method Q, ESI): RT=0.59 min, m+H=154.0; 1H NMR (400 MHz, DMSO) δ: 7.75 (br s, 2H), 4.43 (s, 2H), 3.35 (m, 1H), 2.95 (d, 1H), 1.99 (d, 2H), 1.90 (s, 2H), 1.25 (m, 4H).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-e96752745c3f466fadb5b2bb3ef94964
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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