Sodium cyanoborohydride → HCID 86669069, compound

HRID 1807395Notes

Reaction equation

HRID 1807395 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:16])[CH3:5].C([BH3-])#N.[Na+]>C(O)(=O)C.C(=O)([O-])O.[Na+]>[Cl:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([F:15])[C:9]=1[C@@H:7]1[CH2:8][C@H:6]1[CH:4]([NH:3][O:2][CH3:1])[CH3:5]

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 86669070HCID 86669070, compound

Product 1

HCID 86669069HCID 86669069, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of trans 1-[2-(2-chloro-6-fluoro-phenyl)-cyclopropyl]-ethanone O-methyl-oxime (1.1 g; 4.6 mmol) prepared as described in example P21, in acetic acid (10 ml) at ambient temperature was added portionwise sodium cyanoborohydride (0.60 g; 9.3 mmol). The reaction mixture was stirred for 16 hours at ambient temperature then poured in sodium hydrogen carbonate saturated solution (50 ml) and extracted with dichloromethane (3×50 ml). Combined organic layers were dried over anhydrous sodium sulphate. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel (elution gradient: cyclohexane/ethyl acetate 99:1 to 1:99) to afford 0.85 g (75% of theory) of trans N-{1-[2-(2-chloro-6-fluoro-phenyl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine as a mixture of diastereomeres in form of a clear viscous oil.

Workup

  1. extractionextracted with dichloromethane (3×50 ml)
  2. dry with materialCombined organic layers were dried over anhydrous sodium sulphate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography over silica gel (elution gradient: cyclohexane/ethyl acetate 99:1 to 1:99)

Sources & evidence

ORD record
ord-0f1d7ee1b56d4ba28863cadbe84e3d0e
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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