Tert-butyl (3-methyl-6-carbomethoxy-2-cyclohexen-1-yl)-carbamate → Tert-butyl 3-methyl-6-carboxy-2-cyclohexen-1-yl-carbamate

HRID 326794Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

5 g (18.6 mmol) of tert-butyl (3-methyl-6-carbomethoxy-2-cyclohexen-1-yl)-carbamate are introduced into 40 ml of 1 N sodium hydroxide solution, and the mixture is stirred at 50° C. until a clear solution has formed. The solution is extracted once using diethyl ether, and a pH of 1 is then established at 0° C. using concentrated hydrochloric acid. After the mixture has been extracted using diethyl ether and evaporated, 3.5 g (74% of theory) of tert-butyl 3-methyl-6-carboxy-2-cyclohexen-1-yl-carbamate of melting point 132°-136° C. are obtained. ##STR76##

Workup

customhas formed
extractionThe solution is extracted once using diethyl ether
customis then established at 0° C.
extractionAfter the mixture has been extracted
customevaporated

Sources & evidence

ORD record: ord-6ff3d78edbef4195a06bd21358c7911f
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270340

Reaction notes

Loading…