(3aR,5R,6aR)-Benzyl 5-((3-methoxytetrahydro-2H-pyran-4-yl)amino)-3a-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)hexahydrocyclopenta-[c]pyrrole-2(1H)-carboxylate → ((3aR,5R,6aR)-5-(((3S*,4S*)-3-Methoxytetrahydro-2H-pyran-4-yl)amino)octahydro-cyclopenta[c]pyrrol-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

HRID 571354Notes

Reaction equation

HRID 571354 reaction equation
[CH3:1][O:2][CH:3]1[CH:8]([NH:9][C@@H:10]2[CH2:27][C@H:13]3[CH2:14][N:15](C(OCC4C=CC=CC=4)=O)[CH2:16][C@@:12]3([C:28]([N:30]3[CH2:39][CH2:38][C:37]4[N:36]=[CH:35][C:34]([C:40]([F:43])([F:42])[F:41])=[CH:33][C:32]=4[CH2:31]3)=[O:29])[CH2:11]2)[CH2:7][CH2:6][O:5][CH2:4]1>CO.[Pd]>[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][C@@H:10]2[CH2:27][C@H:13]3[CH2:14][NH:15][CH2:16][C@@:12]3([C:28]([N:30]3[CH2:39][CH2:38][C:37]4[N:36]=[CH:35][C:34]([C:40]([F:43])([F:41])[F:42])=[CH:33][C:32]=4[CH2:31]3)=[O:29])[CH2:11]2)[CH2:7][CH2:6][O:5][CH2:4]1

Participants

4

Reactant 1

HCID 72946982(3aR,5R,6aR)-Benzyl 5-((3-methoxytetrahydro-2H-pyran-4-yl)amino)-3a-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)hexahydrocyclopenta-[c]pyrrole-2(1H)-carboxylate

Product 1

HCID 86708896((3aR,5R,6aR)-5-(((3S*,4S*)-3-Methoxytetrahydro-2H-pyran-4-yl)amino)octahydro-cyclopenta[c]pyrrol-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the product from Step B (1.53 g, 2.55 mmol) in methanol (18 mL) was bubbled with Ar for 15 min, and 10% Palladium on carbon (0.3 g) was added. The mixture was hydrogenated at 25 psi in Parr shaker overnight. Filtration and evaporation to dryness gave the product as yellow foam. 1H-NMR (400 MHz, CDCl3): δ 1.37-2.04 (m, 7H), 2.21 (d, J=5.8 Hz, 1H), 2.47-2.63 (m, 1H), 2.66-2.86 (m, 1H), 2.86-3.54 (m, 12H), 3.60 (br. s., 1H), 3.66-4.21 (m, 4H), 4.61-5.05 (m, 2H), 7.70 (br. s., 1H), 8.71 (br. s., 1H); LC/MS: C23H31F3N4O3: m/z 469.2 (M+H).

Workup

  1. customwas hydrogenated at 25 psi in Parr shaker overnight
  2. filtrationFiltration and evaporation to dryness

Sources & evidence

ORD record
ord-ff79e080d2614d8e8ffa93c78c0f70f5
Source dataset
uspto-grants-2015_05
Patent number
US09024017B2

Reaction notes

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