Potassium Carbonate → Methyl 1-(6-hydroxy-2-naphthoyl)piperidine-4-carboxylate

HRID 525442Notes

Reaction equation

HRID 525442 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([N:17]1[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH3:26])=[O:24])[CH2:19][CH2:18]1)=[O:16])[CH:9]=[CH:8]2)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[OH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([N:17]1[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH3:26])=[O:24])[CH2:19][CH2:18]1)=[O:16])[CH:9]=[CH:8]2

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68279395Methyl 1-(6-acetoxy-2-naphthoyl)piperidine-4-carboxylate

Product 1

HCID 68279553Methyl 1-(6-hydroxy-2-naphthoyl)piperidine-4-carboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 1-(6-acetoxy-2-naphthoyl)piperidine-4-carboxylate (1 g, 2.814 mmol, 1.0 eq), K2CO3 (1.94 g, 14.07 mmol, 5.0 eq) in MeOH (20 mL) was stirred at room temperature for 2 h. The reaction was filtered. The filtrate was concentrated and the residue was purified by prep-HPLC (MeOH: 0.05% TFA/H2O=0-95%) to afford methyl 1-(6-hydroxy-2-naphthoyl)piperidine-4-carboxylate as a white solid (350 mg, yield: 40%). ESI-MS: 314.0 (M+H)+. 1HNMR (400 MHz, DMSO-d6) δ: 9.94 (s, 1H), 7.86-7.84 (m, 2H), 7.73 (d, 1H), 7.38 (d, 1H), 7.16-7.12 (m, 2H), 3.63 (s, 3H), 3.16-2.97 (m, 2H), 2.69-2.63 (m, 3H), 1.96-1.79 (m, 2H), 1.61-1.51 (m, 2H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by prep-HPLC (MeOH: 0.05% TFA/H2O=0-95%)

Sources & evidence

ORD record
ord-1d51d6e1aab84db5b01e13aeb9d8c19f
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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