Hydrochloric Acid → 1-(1-(Ethoxycarbonyl)azepan-4-yl)piperidine-4-carboxylic acid

HRID 714528Notes

Reaction equation

HRID 714528 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-].Cl>C1COCC1>[CH2:22]([O:21][C:19]([N:15]1[CH2:16][CH2:17][CH2:18][CH:12]([N:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)[CH2:13][CH2:14]1)=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89579373Ethyl 4-[4-(ethoxycarbonyl)piperidin-1-yl]azepane-1-carboxylate

Product 1

HCID 895794231-(1-(Ethoxycarbonyl)azepan-4-yl)piperidine-4-carboxylic acidYield 147.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-[4-(ethoxycarbonyl)piperidin-1-yl]azepane-1-carboxylate (1.10 g, 3.4 mmol) was dissolved in THF (60 mL) at rt and 1M LiOH sol. (10 mL) was added. The reaction mixture was stirred at rt for 5 d. 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)piperidine-4-carboxylic acid (1.5 g) as a viscous pale yellow oil, Intermediate 2, which was used crude in subsequent reactions.

Workup

  1. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-d3ea529f161f49c495790f3fb507d7b5
Source dataset
uspto-grants-2015_11
Patent number
US09187451B2

Reaction notes

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