Sodium borohydride → HCID 89852311, compound

HRID 627125Notes

Reaction equation

HRID 627125 reaction equation
O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[Si:12]([O:19][CH2:20][C@@H:21]1[C:26]([CH3:27])=[CH:25][C:24](=[O:28])[CH2:23][N:22]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[BH4-].[Na+]>CO>[Si:12]([O:19][CH2:20][C@@H:21]1[C:26]([CH3:27])=[CH:25][C@H:24]([OH:28])[CH2:23][N:22]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 89852188(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5-oxo-5,6-dihydropyridine-1 (2H)-carboxylate2×

Product 1

HCID 89852311HCID 89852311, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of cerium(III) chloride heptahydrate (6.36 g, 17.07 mmol) and (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 78, 6.07 g, 17.07 mmol) in MeOH (100 mL) at 0° C., sodium tetrahydroborate (0.646 g, 17.07 mmol) was added as a solid. The mixture was stirred at ambient temp for 1 h. The mixture was concentrated and diluted with NH4Cl(aq), H2O and extracted with ether. The ether layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated to give the desired product (5.48 g, 90%) as a yellow oil.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with NH4Cl(aq), H2O
  3. extractionextracted with ether
  4. customThe ether layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7e7b1b9bca3f4ad8b6d41aae16ec6d08
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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