Sodium Hydroxide → 4-(Benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylic acid

HRID 2109485Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([O:22]C)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([OH:22])=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 4-benzyloxycarbonylaminobicyclo[2,2,2]octane-1-carboxylate (64.3 g) was dissolved in ethanol (1100 mL). To this solution, a 1 mol/L aqueous solution of sodium hydroxide (1000 mL) was added and the mixture was stirred at 50° C. for 1 hour. Ethanol in the mixture was evaporated under reduced pressure and the residue was washed with diethylether (500 mL), followed by addition of concentrated hydrochloric acid to adjust the pH to 1. The resulting crystals were filtrated, washed with water, dried under reduced pressure to give 4-benzyloxycarbonylaminobicyclo[2,2,2]octane-1-carboxylic acid (56.1 g).

Workup

customEthanol in the mixture was evaporated under reduced pressure
washthe residue was washed with diethylether (500 mL)
additionfollowed by addition of concentrated hydrochloric acid
filtrationThe resulting crystals were filtrated
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-cfa38ee040764063aeadd614d3df4d66
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514571B2

Reaction notes

Loading…