Sodium borohydride → HCID 131728646, compound

HRID 1362904Notes

Reaction equation

HRID 1362904 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C@@H:8]1[C@@H:13]([C:14]2[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=2[F:22])[CH2:12][CH2:11][N:10]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[C:25]([C:32]([NH2:34])=[O:33])[N:24]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.O1CCCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[C:1]([O:5][C:6](=[O:35])[NH:7][C@@H:8]1[C@@H:13]([C:14]2[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=2[F:22])[CH2:12][CH2:11][N:10]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[C:25]([C:32]([NH2:34])=[O:33])[N:24]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 131728647HCID 131728647, compound

Product 1

HCID 131728646HCID 131728646, compound

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To 993 mg (2.0 mmol) of the product of Step A in 40 mL of 3:1 methanol/tetrahydrofuran at 0° C. was added 166 mg (0.70 mmol) of nickel (II) chloride hexahydrate followed by 318 mg (8.4 mmol) of sodium borohydride in portions over 30 min. The reaction mixture was stirred for an additional 30 min and then quenched with 100 mL of a saturated aqueous sodium bicarbonate solution. The layers were separated and the aqueous phase extracted with three 100-mL portions of 3:1 chloroform/isopropyl alcohol. The combined organic phases were dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to yield a yellow solid which was purified by flash chromatography on a Biotage Horizon® system (silica gel, 0 to 100% ethyl acetate/hexanes gradient) to give the title compound as a yellow crystalline solid. LC/MS 465.6 (M+1).

Workup

  1. customquenched with 100 mL of a saturated aqueous sodium bicarbonate solution
  2. customThe layers were separated
  3. extractionthe aqueous phase extracted with three 100-mL portions of 3:1 chloroform/isopropyl alcohol
  4. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto yield a yellow solid which
  8. customwas purified by flash chromatography on a Biotage Horizon® system (silica gel, 0 to 100% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-60737930be9342e285d3277b0b55d99c
Source dataset
uspto-grants-2011_02
Patent number
US07884104B2

Reaction notes

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