ChemicalBook CAS DataBase List D,L N-Desmethylvenlafaxine

D,L N-Desmethylvenlafaxine synthesis

5synthesis methods

Product Name:D,L N-Desmethylvenlafaxine
CAS Number:149289-30-5
Molecular formula:C16H25NO2
Molecular Weight:263.38

N-FORMYL-1-(2-AMINO-1-(4-METHOXYPHENYL)ETHYL)CYCLOHEXANOL

272788-07-5
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$315.00/10MG

149289-30-5
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$198.00/5mg

Yield: 88.8%

Reaction Conditions:

with dimethylsulfide borane complex in tetrahydrofuran at 0 - 20; for 5 h;Reflux;

Steps:

3
To a solution of crude N-formyl compound (0.585 g, 2.1 mmol) in 6 mL THF was added BH₃.Me₂S (0.480 g, 0.63 mL of 10 M solution, 6.3 mmol) slowly at 0° C. The reaction was allowed to warm to room temperature and then was refluxed for 5 hours. It was cooled to 0° C. and 5 mL of methanol was added very carefully controlling the temperature below 10° C. The reaction was stirred for 10 minutes and volatiles were evaporated off. Residue was partitioned between 3N HCl (20 mL) and ethyl acetate (20 mL). Organic layer was separated and aqueous layer was extracted with ethyl acetate (3×15 mL). Aqueous layer was cooled to 0° C. and was basified by slow addition of conc. NH₄OH. Aqueous layer was saturated with NaCl and was extracted with ethyl acetate (3×20 mL). Combined ethyl acetate layer was dried (Na₂SO₄), ethyl acetate was evaporated in vacuo to give colorless oil (0.493 g, 88.8% yield). (CDCl₃): 7.15 and 6.85 (q, 4H), 3.80 (s, 3H), 3.25 (dd, 1H), 2.95 (dd, 1H), 2.82 (dd, 1H), 2.45 (s, 3H), 1.40 (m, 10H); ¹³C (CDCl₃): 158.4, 133.0, 130.5, 113.7, 73.9, 55.4, 53.8, 53.0, 37.8, 36.5, 33.7, 26.0, 21.9.

References:

Sunovion Pharmaceuticals Inc.;Jerussi, Thomas P.;Senanayake, Chrisantha H.;Bhongle, Nandkumar N. US2015/299102, 2015, A1 Location in patent:Paragraph 0097

593-51-1 Synthesis