Sodium borohydride → (2R,4S)-tert-butyl 2-((1S,2S)-2-amino-1-hydroxy-3-phenylpropyl)-4-fluoropyrrolidine-1-carboxylate

HRID 732354Notes

Reaction equation

HRID 732354 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@@H:9]1[C@@H:14]([OH:26])[C@@H:15]([N+:23]([O-])=O)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@@H:9]1[C@@H:14]([OH:26])[C@@H:15]([NH2:23])[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68814538(2R,4S)-tert-butyl 4-fluoro-2-((1R,2S)-1-hydroxy-2-nitro-3-phenylpropyl)pyrrolidine-1-carboxylate

Product 1

HCID 57838125(2R,4S)-tert-butyl 2-((1S,2S)-2-amino-1-hydroxy-3-phenylpropyl)-4-fluoropyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

Dissolve nickel chloride hexahydrate (0.021 g, 0.09 mmol) and 4-(S)-fluoro-2-(R)-(1-(R)-hydroxy-2-(S)-nitro-3-phenylpropyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.33 g, 0.897 mmol) in methanol (5 mL). Cool in an ice bath and add sodium borohydride (0.17 g, 4.485 mmol) portionwise over 1 min. Stir 10 min, then concentrate. Partition in water and ethyl acetate and filter through filter agent. Separate layers and wash organic layer with saturated aqueous sodium chloride, dry (magnesium sulfate), and concentrate to give the title compound as a white foam.

Workup

  1. temperatureCool in an ice bath
  2. concentrationconcentrate
  3. customPartition in water
  4. filtrationethyl acetate and filter
  5. filtrationthrough filter agent
  6. washSeparate layers and wash organic layer with saturated aqueous sodium chloride
  7. dry with materialdry (magnesium sulfate)
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-e7181558f5304e78acf0c2264c3d1b3a
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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