4-(4-Ethoxycarbonyl-thiophen-2-yl)-piperidine-1-carboxylic acid t-butyl ester → 5-(1-(Tert-butoxycarbonyl)piperidin-4-yl)thiophene-3-carboxylic acid

HRID 1809059Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]([O:21]CC)=[O:20])[CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]([OH:21])=[O:20])[CH:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 130 °C

Procedure

Aqueous sodium hydroxide (1 N, 10 mL) was added to a solution of 4-(4-ethoxycarbonyl-thiophen-2-yl)-piperidine-1-carboxylic acid t-butyl ester (1.0 g) in IMS (10 mL). The reaction was heated at 130° C. for 10 minutes by microwave irradiation. The solution was acidified to pH 7 and the resulting precipitate isolated by filtration and dried under vacuum to give the title compound as a white solid (0.81 g). 1H NMR (400 MHz, CHCl3-d): δ 8.05 (s, 1H), 7.25 (s, 1H), 4.2 (m, 2H), 2.9 (m, 1H), 2.8 (m, 2H), 2.0 (m, 2H), 1.6 (m, 2H), 1.5 (s, 9H).

Workup

customthe resulting precipitate isolated by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-87c4eda05c384d008c2b346e675b205a
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362008B2

Reaction notes

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