(S)-tert-butyl 7-nitro-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate → (S)-tert-Butyl 7-amino-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 339241Notes

Reaction equation

HRID 339241 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][C@@H:9]([C:21](=[O:33])[NH:22][C@H:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)[N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][C@@H:9]([C:21](=[O:33])[NH:22][C@H:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)[N:10]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 86705876(S)-tert-butyl 7-nitro-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 86705875(S)-tert-Butyl 7-amino-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a pressure flask containing 5% Pd/C (91 mg, 0.085 mg) was added a solution of (S)-tert-butyl 7-nitro-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.38 g, 0.85 mmol) in MeOH (8.5 mL). The resulting reaction mixture was stirred under 5 psi H2 for 1 h and then filtered through a pad of CELITE®, rinsing with EtOAc. The filtrate was concentrated in vacuo to give the title compound (301 mg, 84%) as a colorless oil. MS (ESI+) m/z 422.2 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered through a pad of CELITE®
  3. washrinsing with EtOAc
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bacec420aa1a4b84b90d6b6bb1194104
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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