Sodium borohydride → (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-hydroxy-5,6-dihydropyridine-1 (2H)-carboxylate

HRID 627162Notes

Reaction equation

HRID 627162 reaction equation
O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[Si:12]([O:19][CH2:20][C@@H:21]1[CH:26]=[C:25]([C:27](=[O:31])[N:28]([CH3:30])[CH3:29])[C:24](=[O:32])[CH2:23][N:22]1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([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[CH:26]=[C:25]([C:27](=[O:31])[N:28]([CH3:29])[CH3:30])[C@H:24]([OH:32])[CH2:23][N:22]1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 89851837(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate2×

Product 1

HCID 89851842(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-hydroxy-5,6-dihydropyridine-1 (2H)-carboxylateYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of cerium(III) chloride heptahydrate (0.948 g, 2.54 mmol) and (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 134, 1.05 g, 2.54 mmol) in 1 mL MeOH at 0° C., sodium tetrahydroborate (0.096 g, 2.54 mmol) was added as a solid. The mixture was stirred at ambient temp for 15 minutes. The mixture was concentrated and diluted with NH4Cl (aq), H2O and ether. The ether layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated to give the desired product (1.034 g, 98%) as a beige solid.

Workup

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

Sources & evidence

ORD record
ord-5ae751dbdb8642568babc54be59ceea8
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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