N-((S)-6-Pyridin-3-yl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide → N-((S)-6-Piperidin-3-yl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

HRID 1913818Notes

Reaction equation

HRID 1913818 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH2:13][C@@H:12]([NH:17][C:18](=[O:32])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@@H:27]4[CH2:31][CH2:30][CH2:29][O:28]4)=[CH:21][CH:20]=2)[CH2:11][CH2:10]3)[CH:2]=1>[Pt](=O)=O.C(O)(=O)C>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH2:13][C@@H:12]([NH:17][C:18](=[O:32])[C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][C@@H:27]4[CH2:31][CH2:30][CH2:29][O:28]4)=[CH:23][CH:24]=2)[CH2:11][CH2:10]3)[CH2:2]1

Participants

4

Reactant 1

HCID 67544347N-((S)-6-Pyridin-3-yl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Product 1

HCID 59505834N-((S)-6-Piperidin-3-yl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of N-((S)-6-pyridin-3-yl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (0.60 g), glacial acetic acid (30 ml) and platinum(IV) oxide (0.10 g) was stirred vigorously under a hydrogen atmosphere (balloon) for 12 hours. The catalyst was filtered off with suction and the filtrate was concentrated. The product was thus obtained with the molecular weight of 434.58 (C27H34N2O3); MS (ESI): 435 (M+H+).

Workup

  1. filtrationThe catalyst was filtered off with suction
  2. concentrationthe filtrate was concentrated
  3. customThe product was thus obtained with the molecular weight of 434.58 (C27H34N2O3)

Sources & evidence

ORD record
ord-846485c8493d4c1fb2d8e70fc1dde47d
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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