Sodium borohydride → HCID 57126774, compound

HRID 1492012Notes

Reaction equation

HRID 1492012 reaction equation
[C:1]([Si:5]([CH3:25])([CH3:24])[O:6][C@@H:7]1[CH2:11][O:10][C@H:9]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[C@@H:8]1/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[Si:5]([O:6][C@@H:7]1[CH2:11][O:10][C@H:9]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[C@@H:8]1[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86748310HCID 86748310, compound

Product 1

HCID 57126774HCID 57126774, compound

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.93 g (0.0053 mol) of methyl (E)-(2S,3S,4S)-3-[4-(t-butyldimethyl-silyloxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]-2-propenoate and 67 mg (0.28 mmol) of nickel dichloride hexahydrate in 17 ml of methanol is cooled to 0° C. and 0.21 g (0.0054 mol) of sodium borohydride is added in portions over a period of 20 min. The mixture is stirred at 0° C. for another 15 min and at room temperature for 1 h, evaporated to dryness, the residue is triturated with water and ethyl acetate and filtered through a celite bed. The aqueous layer of the filtrate is separated and extracted with ethyl acetate. The combined ethyl acetate extracts are washed with brine, dried (MgSO4) and evaporated to give methyl (2S,3S,4S)-3-[4-(-t-butyldimethylsilyloxy)-2-(3-pyridyl)tetrahydrofurane-3-yl]propanoate as an oil. Flash chromatography of the crude product gave 0.8 g of analytically pure material.

Workup

  1. customevaporated to dryness
  2. customthe residue is triturated with water and ethyl acetate
  3. filtrationfiltered through a celite bed
  4. customThe aqueous layer of the filtrate is separated
  5. extractionextracted with ethyl acetate
  6. washThe combined ethyl acetate extracts are washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-c3e630c48a894cc78e55f90ba38d8ce4
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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