Sodium cyanoborohydride → HCID 86669075, compound

HRID 1807398Notes

Reaction equation

HRID 1807398 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[C:13]([Cl:14])=[C:12]([Cl:15])[S:11][C:10]=1[Cl:16])[CH3:5].C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][NH:3][CH:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[C:13]([Cl:14])=[C:12]([Cl:15])[S:11][C:10]=1[Cl:16])[CH3:5]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 86669076HCID 86669076, compound

Product 1

HCID 86669075HCID 86669075, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of trans 1-[2-(2,4,5-trichloro-thiophen-3-yl)cyclopropyl]-ethanone O-methyl-oxime (2.85 g; 9.5 mmol) prepared as described in example P24, in acetic acid (20 ml) at ambient temperature was added portionwise sodium cyanoborohydride (1.80 g; 29 mmol). The reaction mixture was stirred for 50 hours at ambient temperature then poured on sodium hydroxide solution (0.5M; 150 ml) and extracted with dichloromethane (3×50 ml). Combined organic layers were washed with sodium hydroxide solution (0.5M; 100 ml) and 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 80:20) to afford 1.78 g (62% of theory) of trans O-methyl-N-{1-[2-(2,4,5-trichloro-thiophen-3-yl)-cyclopropyl]-ethyl}-hydroxylamine as a mixture of diastereomeres in form of a yellow oil.

Workup

  1. additionthen poured on sodium hydroxide solution (0.5M; 150 ml)
  2. extractionextracted with dichloromethane (3×50 ml)
  3. washCombined organic layers were washed with sodium hydroxide solution (0.5M; 100 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatography over silica gel (elution gradient: cyclohexane/ethyl acetate 99:1 to 80:20)

Sources & evidence

ORD record
ord-370335133fcc4058ae302fa241196fa5
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

Loading…