Sodium cyanoborohydride → O-methyl-N-[1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethyl]-hydroxylamine

HRID 42731Notes

Reaction equation

[CH3:1][O:2][N:3]=[C:4]([CH:6]1[CH2:11][CH2:10][C:9]([CH3:12])=[CH:8][C:7]1([CH3:14])[CH3:13])[CH3:5].C([BH3-])#N.[Na+]>C(O)(=O)C.ClCCl.[OH-].[Na+]>[CH3:1][O:2][NH:3][CH:4]([CH:6]1[CH2:11][CH2:10][C:9]([CH3:12])=[CH:8][C:7]1([CH3:13])[CH3:14])[CH3:5]

Participants

Conditions

Temperature: 24 °C

Procedure

To a stirred solution of 1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethanone O-methyl-oxime (0.27 g; 1.40 mmol) in acetic acid (3 mL) was added portionwise sodium cyanoborohydride (0.20 g; 3.00 mmol). The reaction mixture was stirred at 24° C. for 16 hours under nitrogen atmosphere. Most of acetic acid was removed under reduced pressure. The yellow sticky oil obtained was dissolved in dichloromethane and poured in 1M sodium hydroxide which was extracted with dichloromethane. Combined organic layers were washed with sodium bicarbonate and dried over sodium sulfate. The solvent was removed in vacuo to afford 0.26 g of colorless oil which was subject to flash-master column chromatography (Elution gradient: cyclohexane/ethyl acetate 99:1 to 80:20) to afford 88 mg (33% of theory) of diastereomer A as a clear oil and 58 mg (22% of theory) of diastereomer B as a clear oil.

Workup

customMost of acetic acid was removed under reduced pressure
customThe yellow sticky oil obtained
extractionwas extracted with dichloromethane
washCombined organic layers were washed with sodium bicarbonate
dry with materialdried over sodium sulfate
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-49e19adf7d1d4c70803acb9d847a9ff4
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536215B2

Reaction notes

Loading…