Water → HCID 57880962, compound

HRID 732378Notes

Reaction equation

HRID 732378 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:14][C@H:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][C@@H:11]1[C@@H:23]([OH:37])[C@@H:24]([N+:34]([O-])=O)[CH2:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].O>CO.[Ni](Cl)Cl>[C:3]([O:7][C:8]([N:10]1[CH2:14][C@H:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][C@@H:11]1[C@@H:23]([OH:37])[C@@H:24]([NH2:34])[CH2:25][C:26]1[CH:27]=[C:28]([F:33])[CH:29]=[C:30]([F:32])[CH:31]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 68814448HCID 68814448, compound

Product 1

HCID 57880962HCID 57880962, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

Add sodium borohydride (0.242 mg, 6.42 mmol) over 1 minute to a solution of (2R,4R)-4-benzyloxy-2-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]pyrrolidine-1-carboxylic acid tert-butyl ester (0.696 g, 1.41 mmol) and nickel (II) chloride (0.29 g, 2.25 mmol) in methanol (30 mL) at room temperature. Stir 20 minutes, add water (3 mL) and evaporate the methanol. Partition the residue with ethyl acetate and water. Filter through a filtering agent, wash with ethyl acetate (300 mL), separate away the aqueous layer, wash with saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate to give the title compound as a colorless oil (619 mg, 95%).

Workup

  1. customevaporate the methanol
  2. customPartition the residue with ethyl acetate and water
  3. filtrationFilter through a filtering agent
  4. washwash with ethyl acetate (300 mL)
  5. customseparate away the aqueous layer
  6. washwash with saturated aqueous sodium chloride
  7. dry with materialdry (magnesium sulfate)
  8. filtrationfilter
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-9fdad846227e4d3698b457b4b632ad9e
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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