Hydrochloric Acid → 1-[1-(Ethoxycarbonyl)azepan-4-yl]-4-methylpiperidine-4-carboxylic acid

HRID 714532Notes

Reaction equation

HRID 714532 reaction equation
[CH3:1][C:2]1([C:20]([O:22]CC)=[O:21])[CH2:7][CH2:6][N:5]([CH:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[Li+].[OH-].Cl>C1COCC1>[CH2:18]([O:17][C:15]([N:11]1[CH2:12][CH2:13][CH2:14][CH:8]([N:5]2[CH2:6][CH2:7][C:2]([CH3:1])([C:20]([OH:22])=[O:21])[CH2:3][CH2:4]2)[CH2:9][CH2:10]1)=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89579337Ethyl 4-[4-methyl-4-(ethoxycarbonyl)piperidin-1-yl]azepane-1-carboxylate

Product 1

HCID 895793081-[1-(Ethoxycarbonyl)azepan-4-yl]-4-methylpiperidine-4-carboxylic acidYield 193.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-[4-methyl-4-(ethoxycarbonyl)piperidin-1-yl]azepane-1-carboxylate (0.37 g, 1.09 mmol) was dissolved in THF (10 mL) at rt and 1M LiOH sol. (3.3 mL) was added. The reaction mixture was stirred at rt overnight. The pH was carefully adjusted to pH 6 by addition of concentrated hydrochloric acid, the solvents were removed in vacuo, to give 1-[1-(ethoxycarbonyl)azepan-4-yl]-4-methylpiperidine-4-carboxylic acid (0.66 g) as a viscous colourless oil, Intermediate 4, which was used crude in subsequent reactions.

Workup

  1. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-ce1544587afc49b6b67ad45a28e5b3af
Source dataset
uspto-grants-2015_11
Patent number
US09187451B2

Reaction notes

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