Sulfuric Acid → HCID 57134866, compound

Cool a solution of lithium aluminum hydride (42.6 mL, 1.0 M in tetrahydrofuran, 42.6 mmol) to about −10° C. Add dropwise a solution of sulfuric acid (2.1 g) in tetrahydrofuran (5 mL) while maintaining the temperature of the reaction mixture at less than 0° C. After 20 minutes, warm to ambient temperature. Add a solution of (S)-2-(3,4-dichlorophenyl)pent-4-enoic acid, N-methyl amide (4.8 g, 18.8 mmol) and tetrahydrofuran (25 mL). After the addition is complete, heat the reaction mixture abbot t 35° C. After 15 hours, cool in an ice bath and carefully quench by the addition of water (5 mL) and tetrahydrofuran (5 mL). Add tetrahydrofuran (60 mL) and filter, and evaporate the filtrate in vacuo to give a residue. Combine the residue and dichloromethane, extract with water, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 1% methanol/dichloromethane, 2% methanol/dichloromethane, 3% methanol/dichloromethane, and 4% methanol/dichloromethane to give (S)-N-methyl-(2-(3,4-dichlorophenyl)pent-4-enyl)amine: Rf=0.54 (silica gel, 9/1/0.1 dichloromethane/methanol/concentrated aqueous ammonia).

1. temperaturewhile maintaining the temperature of the reaction mixture at less than 0° C
2. additionAfter the addition
3. temperatureheat the reaction mixture abbot t 35° C
4. waitAfter 15 hours
5. temperaturecool in an ice bath
6. customcarefully quench by the addition of water (5 mL) and tetrahydrofuran (5 mL)
7. filtrationAdd tetrahydrofuran (60 mL) and filter
8. customevaporate the filtrate in vacuo
9. customto give a residue
10. extractionextract with water
11. dry with materialdry over MgSO4
12. filtrationfilter
13. customevaporate in vacuo
14. customto give a residue

ORD record

ord-3e263055ec0b4dd996fbe223d1145b06

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06316445B1