Hydrochloric Acid → rac-Methyl (1R,2R,4S,5S,6S,7R)-7-aminotricyclo [3.2.2.02,4]nonane-6-carboxylate hydrochloride

HRID 1751269Notes

Reaction equation

C(OC([NH:11][C@@H:12]1[C@@H:18]2[CH:19]=[CH:20][C@@H:14]([C@@H:15]3[C@H:17]2[CH2:16]3)[C@@H:13]1[C:21]([O:23][CH3:24])=[O:22])=O)C1C=CC=CC=1.[ClH:25]>C(OCC)(=O)C.[Pd].C(OCC)C.O1CCOCC1>[ClH:25].[NH2:11][C@@H:12]1[C@@H:18]2[CH2:19][CH2:20][C@@H:14]([C@@H:15]3[C@H:17]2[CH2:16]3)[C@@H:13]1[C:21]([O:23][CH3:24])=[O:22]

Participants

Conditions

Temperature: 25 °C

Procedure

rac-Methyl (1R,2R,4S,5S,6S,7R)-7-{[(benzyloxy)carbonyl]amino}tricyclo[3.2.2.02,4]non-8-ene-6-carboxylate (0.61 g, 1.85 mmol) was dissolved in ethyl acetate (10 mL). 5% Palladium on carbon (0.10 g) was added. The flask was degassed and backfilled with hydrogen gas via balloon. The mixture was stirred at 25° C. for 16 h. The mixture was passed through a plug of Celite and the filtrate was concentrated in vacuo to afford a thick clear oil. The oil was dissolved in diethyl ether (6 mL) and added dropwise, with vigorous stirring, to a mixture of a 4.0M solution of hydrochloric acid in 1,4-dioxane (0.93 mL) in diethyl ether (11 mL). The mixture was concentrated and dried in vacuo to afford the desired product, rac-Methyl (1R,2R,4S,5S,6S,7R)-7-aminotricyclo[3.2.2.02,4]nonane-6-carboxylate hydrochloride (0.43 g, 1.85 mmol, 100%), as a sticky gum. LC-MS (ESI) calcd for C11H17NO2 (free amine) 195.26, found 196.5 [M+H+].

Workup

customThe flask was degassed
concentrationthe filtrate was concentrated in vacuo
customto afford a thick clear oil
concentrationThe mixture was concentrated
customdried in vacuo

Sources & evidence

ORD record: ord-0de24dac0009478595316a125f697c01
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156832B2

Reaction notes

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