Trifluoroacetic acid → HCID 67384925, compound

HRID 2360972Notes

Reaction equation

HRID 2360972 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]([C:11]2([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=3)[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[O:10])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:4]1([CH2:7][O:8][C:9]([C:11]2([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([C:31]#[N:32])=[CH:29][CH:30]=3)[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)=[O:10])[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67385108HCID 67385108, compound

Product 1

HCID 67384925HCID 67384925, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-cyano-benzyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-cyclohexylmethyl ester (3.90 mmol; 1.72 g) in dichloromethane (12 mL) at 0° C. was added trifluoroacetic acid (12 mL) and the resulting mixture was stirred for 2 hours at room temperature. The resulting mixture was evaporated. The resulting residue was dissolved in ethyl acetate (50 mL) and washed with a saturated sodium bicarbonate solution (25 mL) and brine (25 mL). The organic phase was dried over magnesium sulfate, filtered, and evaporated to yield 4-(4-cyano-benzyl)-piperidine-4-carboxylic acid cyclohexylmethyl ester. 1H-NMR (CDCl3): 7.55 (1H, d), 7.20 (1H, d), 3.90 (2H, dd), 3.35 (2H, m), 2.70-3.10 (3H, m), 2.60 (1H, m), 2.25 (1H, m), 0.70-2.20 (15H, m).

Workup

  1. customThe resulting mixture was evaporated
  2. dissolutionThe resulting residue was dissolved in ethyl acetate (50 mL)
  3. washwashed with a saturated sodium bicarbonate solution (25 mL) and brine (25 mL)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e19241600dfb4da58e9c3e5e0fb69503
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

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