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

HRID 714542Notes

Reaction equation

HRID 714542 reaction equation
[CH3:1][O:2][C:3]1([C:21]([O:23]C)=[O:22])[CH2:8][CH2:7][N:6]([CH:9]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1.[Li+].[OH-].Cl>C1COCC1>[CH2:19]([O:18][C:16]([N:12]1[CH2:13][CH2:14][CH2:15][CH:9]([N:6]2[CH2:5][CH2:4][C:3]([O:2][CH3:1])([C:21]([OH:23])=[O:22])[CH2:8][CH2:7]2)[CH2:10][CH2:11]1)=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89579395Ethyl 4-[4-methoxy-4-(methoxycarbonyl)piperidin-1-yl]azepane-1-carboxylate

Product 1

HCID 895794691-[1-(Ethoxycarbonyl)azepan-4-yl]-4-methoxypiperidine-4-carboxylic acidYield 102.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-[4-methoxy-4-(methoxycarbonyl)piperidin-1-yl]azepane-1-carboxylate (0.136 g, 0.39 mmol) was dissolved in THF (5 mL) at rt and 1M LiOH sol. (0.4 mL) was added. The reaction mixture was stirred at rt for 2 days. 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-methoxypiperidine-4-carboxylic acid (0.131 g), Intermediate 8, as a yellow oil which was used directly without further purification.

Workup

  1. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-a415d3e58e664121892e9d481b0f47a2
Source dataset
uspto-grants-2015_11
Patent number
US09187451B2

Reaction notes

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