Hydrochloric Acid → 1-[8-(Ethoxycarbonyl)-8-azabicyclo[3.2.1]oct-3-yl]-4-methoxypiperidine-4-carboxylic acid

HRID 1777287Notes

Reaction equation

HRID 1777287 reaction equation
[CH3:1][O:2][C:3]1([C:22]([O:24]C)=[O:23])[CH2:8][CH2:7][N:6]([CH:9]2[CH2:15][CH:14]3[N:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:11]([CH2:12][CH2:13]3)[CH2:10]2)[CH2:5][CH2:4]1.[Li+].[OH-].Cl>C1COCC1>[CH2:20]([O:19][C:17]([N:16]1[CH:11]2[CH2:12][CH2:13][CH:14]1[CH2:15][CH:9]([N:6]1[CH2:7][CH2:8][C:3]([O:2][CH3:1])([C:22]([OH:24])=[O:23])[CH2:4][CH2:5]1)[CH2:10]2)=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 90079548Ethyl 3-[4-methoxy-4-(methoxycarbonyl)piperidin-1-yl]-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 900796311-[8-(Ethoxycarbonyl)-8-azabicyclo[3.2.1]oct-3-yl]-4-methoxypiperidine-4-carboxylic acidYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isomer 1 of ethyl 3-[4-methoxy-4-(methoxycarbonyl)piperidin-1-yl]-8-azabicyclo[3.2.1]octane-8-carboxylate (0.097 g, 0.27 mmol) was dissolved in THF (5 mL) at rt and 1 M LiOH sol. (0.3 mL) was added. The reaction mixture was stirred at rt for 7 days. The pH was carefully adjusted to pH 6 by addition of concentrated hydrochloric acid, the solvents were removed in vacuo, to give 1-[8-(ethoxycarbonyl)-8-azabicyclo[3.2.1]oct-3-yl]-4-methoxypiperidine-4-carboxylic acid (0.093 g, 100%) as an off white solid.

Workup

  1. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-eb81e373dbf04623b93711f34e834601
Source dataset
uspto-grants-2016_02
Patent number
US09266857B2

Reaction notes

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