Trifluoroacetic acid → HCID 178495632, compound

HRID 1257697Notes

Reaction equation

HRID 1257697 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][O:15][CH3:16])[CH2:10][CH2:9]1)(C)(C)C.[F:18][C:19]([F:24])([F:23])[C:20]([OH:22])=[O:21]>C(Cl)Cl>[F:18][C:19]([F:24])([F:23])[C:20]([OH:22])=[O:21].[CH3:16][O:15][CH2:14][C@H:11]1[CH2:12][CH2:13][C@H:8]([NH2:7])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178495641HCID 178495641, compound

Product 1

HCID 178495632HCID 178495632, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of trans (4-methoxymethyl-cyclohexyl)-carbamic acid tert-butyl ester (1.41 g, 5.80 mmol) in DCM (12 mL) was treated with trifluoroacetic acid (4 mL). The mixture was stirred for 1 hour then concentrated under vacuum. The residue was taken into ether and concentrated under vacuum a total of five times to afford 1.88 g of crude trans 4-methoxymethyl-cyclohexylamine trifluoroacetic acid salt as a colourless residue. This was not purified further. 1H NMR (400 MHz, CDCl3): δ 7.48 (br s, 3H), 3.34 (s, 3H), 3.22 (d, 2H), 3.15-3.00 (m, 1H), 2.11-2.00 (m, 2H), 1.94-1.83 (m, 2H), 1.65-1.50 (m, 1H), 1.46-1.31 (m, 2H), 1.13-0.96 (m, 2H).

Workup

  1. concentrationthen concentrated under vacuum
  2. concentrationconcentrated under vacuum a total of five times

Sources & evidence

ORD record
ord-497f6c4afe054d4690ac3f351802ecca
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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