HCID 66731937, compound → HCID 66732120, compound

HRID 1963281Notes

Reaction equation

HRID 1963281 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]([OH:13])=[O:12])[CH2:7][CH:6]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)=[O:4]>CC(OC)(C)C>[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][C@@H:6]1[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=1)=[O:4]

Participants

3

Reactant 1

HCID 66731937HCID 66731937, compound

Product 1

HCID 66732120HCID 66732120, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

1-(Methoxycarbonyl)-2-(4-(trifluoromethyl)benzyl)piperidine-4-carboxylic acid (14.65 g, 42.43 mmol) was suspended in MTBE (150 mL) and heated under reflux for 1 min, then stirred at room temperature for 3 days. The solids were isolated and dried under vacuum. Cis-1-(methoxycarbonyl)-2-(4-(trifluoromethyl)benzyl)piperidine-4-carboxylic acid (9.3 g, 63.5%) was isolated. 1H NMR (600 MHz, cd3od) δ 1.68-1.77 (m, 1H), 1.90-1.97 (m, 1H), 1.99-2.10 (m, 2H), 2.58-2.64 (m, 1H), 2.83-2.89 (m, 1H), 2.93-3.00 (m, 1H), 3.16-3.31 (m, 1H), 3.43 (s, 3H), 3.86-3.92 (m, 1H), 4.31-4.36 (m, 1H), 7.36 (d, 2H), 7.53 (d, 2H).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 min
  3. customThe solids were isolated
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f62922a343c049dbaea972653d4629bd
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…