Triethylamine → HCID 66732042, compound

HRID 1963296Notes

Reaction equation

HRID 1963296 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:24]=[CH:23][C:7]([CH2:8][CH:9]2[CH2:14][CH:13]([C:15]([O:17]C)=[O:16])[CH2:12][CH2:11][N:10]2[C:19]([O:21][CH3:22])=[O:20])=[CH:6][CH:5]=1.[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>CC#N.O>[CH3:22][O:21][C:19]([N:10]1[CH2:11][CH2:12][CH:13]([C:15]([OH:17])=[O:16])[CH2:14][CH:9]1[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:25])([F:26])[F:1])=[CH:24][CH:23]=1)=[O:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66735198HCID 66735198, compound

Product 1

HCID 66732042HCID 66732042, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of dimethyl 2-(4-(trifluoromethoxy)benzyl)piperidine-1,4-dicarboxylate (9.72 g, 25.90 mmol) in MeCN (80 mL) and water (1.6 mL) was added lithium bromide (18.2 g, 209.57 mmol) and triethylamine (15 mL, 108.21 mmol). The resulting mixture was heated under reflux for 3 h, then cooled to room temperature. Water and MTBE were added. The organic phase was extracted with water twice. The pooled aqueous layers were adjusted to pH 1 with 3.8 M HCl and then extracted with DCM (3×). The mixture was filtered through a diatomeous earth filter carton. The combined organic layers were dried over MgSO4 and evaporated. 1-(Methoxycarbonyl)-2-(4-(trifluoromethoxy)benzyl)piperidine-4-carboxylic acid (8.75 g, 94%) was isolated as a pale yellow solid. MS m/z 360 (M−H)−

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 h
  3. extractionThe organic phase was extracted with water twice
  4. extractionextracted with DCM (3×)
  5. filtrationThe mixture was filtered through a diatomeous earth
  6. filtrationfilter carton
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-254f34a4ccf1442bafa6a84edc665b43
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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