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

HRID 714530Notes

Reaction equation

HRID 714530 reaction equation
[F: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[CH2:4][CH2:3][C:2]([F:1])([C:20]([OH:22])=[O:21])[CH2:7][CH2:6]2)[CH2:9][CH2:10]1)=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89579328Ethyl 4-[4-fluoro-4-(ethoxycarbonyl)piperidin-1-yl]azepane-1-carboxylate

Product 1

HCID 895795461-[1-(Ethoxycarbonyl)azepan-4-yl]-4-fluoropiperidine-4-carboxylic acidYield 148.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-[4-fluoro-4-(ethoxycarbonyl)piperidin-1-yl]azepane-1-carboxylate (2.26 g, 6.85 mmol) was dissolved in THF (60 mL) at rt and 1M LiOH sol. (6.5 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-fluoropiperidine-4-carboxylic acid (3.21 g) as a white waxy solid, Intermediate 3, which was used crude in subsequent reactions.

Workup

  1. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-8e3a20a5d77c4f428cd3c62235d346d6
Source dataset
uspto-grants-2015_11
Patent number
US09187451B2

Reaction notes

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