Methanol → HCID 117988308, compound

HRID 2206060Notes

Reaction equation

HRID 2206060 reaction equation
[C:1]([C:4]1[S:8][CH:7]=[C:6]([C:9]2[C:13]3[C:14](=[O:22])[NH:15][CH:16]=[C:17]([C:18](OC)=[O:19])[C:12]=3[N:11]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:10]=2)[CH:5]=1)(=[O:3])[NH2:2].C1COCC1.CO.[BH4-].[Li+]>O>[CH:23]1([N:11]2[C:12]3[C:17]([CH2:18][OH:19])=[CH:16][NH:15][C:14](=[O:22])[C:13]=3[C:9]([C:6]3[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[S:8][CH:7]=3)=[CH:10]2)[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 117988420HCID 117988420, compound

Product 1

HCID 117988308HCID 117988308, compoundYield 28.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 3-(5-carbamoyl-3-thienyl)-1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (30 mg) obtained in Example 34 in a mixed solvent of THF (0.5 mL) and methanol (0.5 mL) was added lithium borohydride (4.4 mg), and the mixture was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a2a40e2dfe3e408caccaf2f2a0ca42d0
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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