Ethanol → HCID 57563474, compound

HRID 507784Notes

Reaction equation

HRID 507784 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][C:8]=1[N:21]([CH2:23][CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)[CH3:22])[CH3:2].C(O)C.[BH4-].[Na+]>O1CCCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[CH2:1]([O:3][C:4](=[O:35])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:9][C:8]=1[N:21]([CH2:23][CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)[CH3:22])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 68465956HCID 68465956, compound

Product 1

HCID 57563474HCID 57563474, compound

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound prepared in Example 23 (135 mg) in tetrahydrofuran (1.2 ml)-ethanol (0.3 ml) were added portionwise nickel chloride hexahydrate (70 mg) and sodium borohydride (45 mg) at 0° C. The mixture was stirred for 15 minutes. The reaction mixture was extracted with diethyl ether. The organic layer was filtered. The filtrate was extracted with diethyl ether. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give the title compound having the following physical data.

Workup

  1. extractionThe reaction mixture was extracted with diethyl ether
  2. filtrationThe organic layer was filtered
  3. extractionThe filtrate was extracted with diethyl ether
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-138f87a5ee574faa883db34dada6a163
Source dataset
uspto-grants-2010_08
Patent number
US07786161B2

Reaction notes

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