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Sodium borohydride → (2S,5R)-5-[(1S,2S)-2-Amino-3-(3,5-difluoro-phenyl)-1-hydroxypropyl]-2-ethoxymorpholine-4-carboxylic acid tert-butyl ester

HRID 20341
Notes
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Reaction equation

HRID 20341 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[C@@H:15]([C@@H:16]([OH:30])[C@@H:17]([N+:27]([O-])=O)[CH2:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)[CH2:14][O:13][C@H:12]([O:31][CH2:32][CH3:33])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO.[Ni](Cl)Cl>[C:3]([O:7][C:8]([N:10]1[C@@H:15]([C@@H:16]([OH:30])[C@@H:17]([NH2:27])[CH2:18][C:19]2[CH:20]=[C:21]([F:26])[CH:22]=[C:23]([F:25])[CH:24]=2)[CH2:14][O:13][C@H:12]([O:31][CH2:32][CH3:33])[CH2:11]1)=[O:9])([CH3:5])([CH3:6])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68561117(2S,5R)-5-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2-ethoxymorpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 68562756(2S,5R)-5-[(1S,2S)-2-Amino-3-(3,5-difluoro-phenyl)-1-hydroxypropyl]-2-ethoxymorpholine-4-carboxylic acid tert-butyl esterYield 70.2%

Reagents, catalysts & solvents 2

HCID 24385Nickel Dichloride
Catalyst
HCID 887MethanolSolvent

Procedure

Add sodium borohydride (0.061 g, 1.62 mmol) portionwise to a solution of (2S,5R)-5-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2-ethoxymorpholine-4-carboxylic acid tert-butyl ester (0.145 g, 0.325 mmol) and nickel (II) chloride (0.063 g, 0.487 mmol) at room temperature in methanol (5 mL) and stir 30 for min. Add water (˜3 mL) and concentrate. Dilute with ethyl acetate and filter through a filtering agent. Partition the filtrate between ethyl acetate and water, dry (magnesium sulfate) and concentrate to give the title compound as a white solid (95 mg, 70%).

Workup

  1. concentrationAdd water (˜3 mL) and concentrate
  2. additionDilute with ethyl acetate
  3. filtrationfilter through a filtering agent
  4. customPartition the filtrate between ethyl acetate and water
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-c600e7253e0e4dd79af57879c261dd45
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745438B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes