Tetrahydrofuran → HCID 67182915, compound

HRID 84016Notes

Reaction equation

HRID 84016 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C@H:10]2[O:19][C@H:13]3[O:14][C:15]([CH3:18])([CH3:17])[O:16][C@H:12]3[C@H:11]2[CH2:20][CH2:21][N:22]2[C:27](=[O:28])[C:26]3[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=3[N:24]=[N:23]2)=[CH:4][CH:3]=1.O1CCCC1>[Pd].CO>[CH3:17][C:15]1([CH3:18])[O:14][C@@H:13]2[O:19][C@H:10]([CH2:9][CH2:8][C:5]3[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=3)[C@H:11]([CH2:20][CH2:21][N:22]3[C:27](=[O:28])[C:26]4[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=4[N:24]=[N:23]3)[C@@H:12]2[O:16]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 671828143-(2-{(3aS,5R,6S,6aS)-5-[(E)-2-(4-bromophenyl)vinyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}ethyl)-1,2,3-benzotriazin-4(3H)-one

Product 1

HCID 67182915HCID 67182915, compoundYield 118.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the solution of the compound obtained from step j of Example 1 (0.3 g) in a solvent mixture of tetrahydrofuran:methanol (10 mL:10 mL) palladium/carbon (0.2 g, 10%) was added at room temperature, and the reaction mixture was hydrogenated at 35 psi for 4 hours in a Paar apparatus. The reaction mixture was filtered through a celite pad and the residue was washed with methanol. The filtrate was concentrated to afford the title compound (0.3 g).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washthe residue was washed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6d4c9e0764ad4debbb9b91b333d0b574
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Reaction notes

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