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

HRID 714538Notes

Reaction equation

HRID 714538 reaction equation
[CH3:1][O:2][C:3]1([C:23]([O:25]C)=[O:24])[CH2:8][CH2:7][N:6]([CH:9]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1.[Li+].[OH-].Cl>C1COCC1>[C:19]([O:18][C:16]([N:12]1[CH2:13][CH2:14][CH2:15][CH:9]([N:6]2[CH2:7][CH2:8][C:3]([O:2][CH3:1])([C:23]([OH:25])=[O:24])[CH2:4][CH2:5]2)[CH2:10][CH2:11]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 117678494Tert-butyl 4-[4-methoxy-4-(methoxycarbonyl)piperidin-1-yl]azepane-1-carboxylate

Product 1

HCID 1176784071-[1-(Tert-butoxycarbonyl)azepan-4-yl]-4-methoxypiperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-butyl 4-[4-methoxy-4-(methoxycarbonyl)piperidin-1-yl]azepane-1-carboxylate (0.06 g, 0.17 mmol) was dissolved in THF (5 mL) at rt and 1M LiOH sol. (0.35 mL) was added. The reaction mixture was stirred at rt for 8 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-(tert-butoxycarbonyl)azepan-4-yl]-4-methoxypiperidine-4-carboxylic acid which was used crude in subsequent reaction.

Workup

  1. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-639f83b1669f4dc789a008ca93a3e80e
Source dataset
uspto-grants-2015_11
Patent number
US09187451B2

Reaction notes

Loading…