rac-Methyl (1R,2R,4S,5S,6R,7S)-7-{[(benzyloxy)carbonyl]amino}tricyclo [3.2.2.02,4]non-8-ene-6-carboxylate → rac-Methyl (1R,2R,4S,5S,6R,7S)-7-aminotricyclo[3.2.2.02,4]nonane-6-carboxylate

HRID 1751274Notes

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>C(OCC)(=O)C.[Pd]>[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,6R,7S)-7-{[(benzyloxy)carbonyl]amino}tricyclo[3.2.2.02,4]non-8-ene-6-carboxylate (0.35 g, 1.07 mmol) was dissolved in ethyl acetate (10 mL). 5% Palladium on carbon (0.04 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 the crude product, rac-Methyl (1R,2R,4S,5S,6R,7S)-7-aminotricyclo[3.2.2.02,4]nonane-6-carboxylate, as a thick clear oil, which was used in the next step without further purification. LC-MS (ESI) calcd for C11H17NO2 (free amine) 195.26, found 196.3 [M+H+].

Workup

customThe flask was degassed
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-4aa1344d84924603b8a5a5446a25eb33
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156832B2

Reaction notes

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