Methanol → HCID 118557986, compound

HRID 2207253Notes

Reaction equation

HRID 2207253 reaction equation
[Br-].[Br:2][C:3]1[CH:4]=[N+:5]([CH2:24][C:25]2[CH:26]=[C:27](C)[CH:28]=[CH:29][CH:30]=2)[CH:6]=[CH:7][C:8]=1[CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:21][CH3:22])=[C:15]([O:19][CH3:20])[CH:16]=2)[C:11]1=[O:23].[BH4-].[Na+].[CH3:34]O>C1COCC1>[Br:2][C:3]1[CH2:4][N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:34])[CH:6]=[CH:7][C:8]=1[CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:21][CH3:22])=[C:15]([O:19][CH3:20])[CH:16]=2)[C:11]1=[O:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 118557920HCID 118557920, compound

Product 1

HCID 118557986HCID 118557986, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 146 (45 mg, 0.08 mmol) in a mixture of methanol and THF (5 mL, respectively 1:4) was added sodium borohydride (3 mg, 1 equiv) in one portion at 0° C. The reaction mixture was then stirred at this temperature for 1 h and quenched with 35% aqueous ammonia solution (3 mL). The mixture was extracted with dichloromethane (3×) and the organic phase was dried over magnesium sulfate, filtered and concentrated to dryness. The crude residue was purified by column chromatography on silica gel (petroleum ether/EtOAc: 2/3) to afford the title compound 168 as a yellow solid (Yield 21.9 mg, 60%).

Workup

  1. customquenched with 35% aqueous ammonia solution (3 mL)
  2. extractionThe mixture was extracted with dichloromethane (3×)
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude residue was purified by column chromatography on silica gel (petroleum ether/EtOAc: 2/3)

Sources & evidence

ORD record
ord-710272b0f4f54975bad9849014c01af4
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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