Sodium Bicarbonate → HCID 86669067, compound

HRID 1807394Notes

Reaction equation

HRID 1807394 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])[CH3:5].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][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 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 86669068HCID 86669068, compound

Product 1

HCID 86669067HCID 86669067, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of trans 1-[2-(2-chloro-phenyl)-cyclopropyl]-ethanone O-methyl-oxime (1.1 g; 5 mmol) prepared as described in example P19 in acetic acid (10 ml) at ambient temperature was added portionwise sodium cyanoborohydride (0.65 g; 10 mmol). The reaction mixture was stirred for 16 hours at ambient temperature then poured on saturated sodium hydrogen carbonate 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 0.33 g (30% of theory) trans N-{1-[2-(2-Chloro-phenyl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine diastereomer A as a clear viscous oil and 0.46 g (41% of theory) and trans N-{1-[2-(2-Chloro-phenyl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine diastereomer B as 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-b31b0caeaed44f8c9d5719ac4015dac3
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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