Trifluoroacetic acid → HCID 178457231, compound

HRID 2057259

Reaction equation

HRID 2057259 reaction equation
C(O[C:6](=O)[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17][N:18]([CH2:20][CH:21]=[CH2:22])[CH3:19])[CH2:11][CH2:10]1)C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:20]([N:18]([CH3:19])[CH2:17][C:16]#[C:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([NH:7][CH3:6])[CH2:10][CH2:11]1)[CH:21]=[CH2:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178457235HCID 178457235, compound

Product 1

HCID 178457231HCID 178457231, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 200 mg (0.62 mmol) of trans-{4-[3-(Allyl-methyl-amino)-prop-1-ynyl]-cyclohexyl}-methyl-carbamic acid tert-butyl ester in 3.5 ml CH2Cl2 was treated at 0° C. with 1.7 ml TFA (for 20 min). After 30 min at this temperature, the reaction mixture was evaporated, treated with 1 N NaOH/CH2Cl2 (3×). The organic phase was dried over Na2SO4 and evaporated to yield 147 mg (quantitative) of trans-{4-[3-(Allyl-methyl-amino)-prop-1-ynyl]-cyclohexyl}-methyl-amine, MS: 221 (MH+).

Workup

  1. customthe reaction mixture was evaporated
  2. additiontreated with 1 N NaOH/CH2Cl2 (3×)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-1c2d83f85a1f46abb6b84ef524980d7a
Source dataset
uspto-grants-2008_02
Patent number
US07335687B2

Linked notes

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