Trifluoroacetic acid → HCID 71237318, compound

HRID 2280716Notes

Reaction equation

HRID 2280716 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([NH:9]C(=O)OC(C)(C)C)[CH2:4]1.[C:17]([OH:23])([C:19]([F:22])([F:21])[F:20])=[O:18]>C(Cl)Cl>[F:20][C:19]([F:22])([F:21])[C:17]([OH:23])=[O:18].[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([NH2:9])[CH2:4]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86676337Carbamic acid, N-[(1R,3S)-3-methoxycyclohexyl]-, 1,1-dimethylethyl ester

Product 1

HCID 71237318HCID 71237318, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (1R,3S)-3-methoxycyclohexylcarbamate (1.0686 g, 4.66 mmol) in anhydrous DCM (18.64 mL) was added TFA (3.59 mL, 46.6 mmol) and the resulting solution was stirred at room temperature for 1 h. After that, the solvents were removed in vacuo, and the resulting residue was triturated with ethyl ether (2×50 mL) to afford (1R,3S)-3-methoxycyclohexanamine trifluoroacetate (1.133 g, 4.66 mmol, 100% yield) as a white solid. The crude product was used without further purification in the next step.

Workup

  1. customAfter that, the solvents were removed in vacuo
  2. customthe resulting residue was triturated with ethyl ether (2×50 mL)

Sources & evidence

ORD record
ord-5b0d936ef609453584e5b0e215ea8144
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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