Sodium cyanoborohydride → trans N-{1-[2-(5-chloro-thiophen-2-yl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine
Reaction equation
[CH3:1][O:2][N:3]=[C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[S:10][C:11]([Cl:14])=[CH:12][CH:13]=1)[CH3:5].C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:14][C:11]1[S:10][C:9]([C@@H:7]2[CH2:8][C@H:6]2[CH:4]([NH:3][O:2][CH3:1])[CH3:5])=[CH:13][CH:12]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of trans 1-[2-(5-Chloro-thiophen-2-yl)cyclopropyl]-ethanone O-methyl-oxime (1.2 g; 5.2 mmol) prepared as described in example P25, in acetic acid (15 ml) at ambient temperature was added portionwise sodium cyanoborohydride (1.0 g; 15.7 mmol). The reaction mixture was stirred for 16 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 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 50:50) to afford 0.91 g (79% of theory) of trans N-{1-[2-(5-chloro-thiophen-2-yl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine as a mixture of diastereomeres in form of a clear viscous oil.
Workup
- additionthen poured on sodium hydroxide solution (0.5M; 150 ml)
- extractionextracted with dichloromethane (3×50 ml)
- dry with materialCombined organic layers were dried over anhydrous sodium sulphate
- customThe solvent was removed in vacuo
- customthe residue was purified by flash chromatography over silica gel (elution gradient: cyclohexane/ethyl acetate 99:1 to 50:50)
Sources & evidence
- ORD record
- ord-b8f5968b79fc4d338df4cdcc91308f11
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357635B2
Reaction notes
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