Sodium borohydride → HCID 68818204, compound

HRID 1436526Notes

Reaction equation

HRID 1436526 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]([CH:14]([OH:26])[CH:15]([N+:23]([O-])=O)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]2[CH:27]([CH2:28][O:29][CH3:30])[CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.[Ni](Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH:13]([CH:14]([OH:26])[CH:15]([NH2:23])[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]2[CH:27]([CH2:28][O:29][CH3:30])[CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 69015226HCID 69015226, compound

Product 1

HCID 68818204HCID 68818204, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

Cool a mixture of 3-(1-hydroxy-2-nitro-3-phenylpropyl)-7-methoxymethyl-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.320 g, 0.761 mmol) and nickel (II) chloride (0.150 g, 1.14 mmol) in methanol (10 mL) in a water bath and slowly add sodium borohydride (0.115 g, 3.04 mmol). After 5 min, quench the reaction with water and concentrate. Add ethyl acetate and water, then filter through a filtering agent and wash solid with ethyl acetate. Separate the layers and wash organic layer with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound (0.243 g, 82%).

Workup

  1. temperatureCool
  2. customquench
  3. customthe reaction with water
  4. concentrationconcentrate
  5. filtrationAdd ethyl acetate and water, then filter through a filtering agent
  6. washwash solid with ethyl acetate
  7. customSeparate the layers
  8. washwash organic layer with saturated aqueous sodium chloride
  9. dry with materialdry (magnesium sulfate)
  10. concentrationconcentrate

Sources & evidence

ORD record
ord-2da27fac6da34ad2803baaf2bbaca6ad
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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