HCID 69937347, compound → HCID 69937537, compound

HRID 2281849Notes

Reaction equation

HRID 2281849 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C@:11]12[CH2:19][O:18][C@H:17]([CH3:20])[C@H:16]1[C:15](=[O:21])[N:14]([CH3:22])[C:13]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[N:12]2.[H][H]>C(O)C.[Pd]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C@:11]23[CH2:19][O:18][C@H:17]([CH3:20])[C@H:16]2[C:15](=[O:21])[N:14]([CH3:22])[C:13]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[N:12]3)[CH:4]=1

Participants

5

Reactant 2

HCID 69937347HCID 69937347, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69937537HCID 69937537, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl ((4aS,5R,7aS)-7a-(2-fluoro-5-nitrophenyl)-3,5-dimethyl-4-oxo-3,4,4a,5,7,7a-hexahydrofuro[3,4-d]pyrimidin-2-yl)carbamate (1.6 g, 3.77 mmol) in ethanol (30 ml) was hydrogenated over 10% Pd/C (200 mg) at RT under a balloon of hydrogen for 4 h. The catalyst was removed by filtration through Celite-washing with ethanol. The filtrate was evaporated to give the title compound (1.48 g, colourless foam). 1H NMR (400 MHz, CDCl3) δ ppm 1.50 (d, J=6.06 Hz, 3H) 1.54 (s, 9H) 3.29 (s, 3H) 3.35 (dd, J=9.22, 1.89 Hz, 1H) 3.63 (s, 2H) 4.25-4.30 (m, 1H) 4.33-4.42 (m, 2H) 6.44 (dd, J=6.32, 2.78 Hz, 1H) 6.56-6.63 (m, 1H) 6.91 (dd, J=10.99, 8.72 Hz, 1H) 10.47 (br. s., 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. washthrough Celite-washing with ethanol
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-f0715ee75577491b90d5065a5fa23cef
Source dataset
uspto-grants-2015_09
Patent number
US09139594B2

Reaction notes

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