Water → HCID 68815117, compound

HRID 732369Notes

Reaction equation

HRID 732369 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[CH2:10][C@@H:9]1[C@@H:22]([OH:36])[C@@H:23]([N+:33]([O-])=O)[CH2:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[CH2:10][C@@H:9]1[C@@H:22]([OH:36])[C@@H:23]([NH2:33])[CH2:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 68814384HCID 68814384, compound

Product 1

HCID 68815117HCID 68815117, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add to a solution of (2R,4R)-2-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-4-(3-methoxy-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (276 mg, 0.54 mmol) in methanol (9 mL) nickel (II) chloride followed by sodium borohydride (0.082 g, 2.17 mmol). Stir reaction for 15 min, add water (1 mL) and concentrate. Partition with ethyl acetate and water and filter through a filtering agent. Rinse cake with ethyl acetate. Separate layers, dry (magnesium sulfate) and concentrate to give the title compound as a white solid (0.244 g, 94%).

Workup

  1. customreaction for 15 min
  2. concentrationconcentrate
  3. customPartition with ethyl acetate and water
  4. filtrationfilter through a filtering agent
  5. washRinse cake with ethyl acetate
  6. dry with materialSeparate layers, dry (magnesium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-ba0e82bb65fc46a986f03d784ebb25f5
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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