(+/-)-8-[5-(1-Ethoxycarbonyl-ethyl)-2-methoxy-phenyl]-5-fluoro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester → (+/-)-Ethyl 2-(3-(5-fluoro-1,2,3,4-tetrahydroisoquinolin-8-yl)-4-methoxyphenyl)propanoate

HRID 1773993Notes

Reaction equation

C(OC([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[C:14]([C:22]3[CH:27]=[C:26]([CH:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:29])[CH:25]=[CH:24][C:23]=3[O:35][CH3:36])[CH:15]=[CH:16][C:17]=2[F:21])[CH2:12]1)=O)C1C=CC=CC=1>CCO.[Pd]>[F:21][C:17]1[CH:16]=[CH:15][C:14]([C:22]2[CH:27]=[C:26]([CH:28]([CH3:29])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:25]=[CH:24][C:23]=2[O:35][CH3:36])=[C:13]2[C:18]=1[CH2:19][CH2:20][NH:11][CH2:12]2

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution under N2 of (±)-8-[5-(1-ethoxycarbonyl-ethyl)-2-methoxy-phenyl]-5-fluoro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (57 mg, 0.12 mmol, 1 eq.) in EtOH (40 mL), palladium on activated carbon (10 wt. %, 3.2 mg) was added. The flask was evacuated and backfilled with H2 (3×). The black suspension was stirred at 50° C. under an H2-atmosphere for 18 hours. The suspension was filtered through Celite, the Celite rinsed with EtOH. The filtrate was concentrated in vacuo to afford the title product as a yellow oil. The product was used without further purification.

Workup

customThe flask was evacuated
filtrationThe suspension was filtered through Celite
washthe Celite rinsed with EtOH
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-eb1e365ad83b424c9f8e2e4516acbefe
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255090B2

Reaction notes

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