Water → 4-Amino-4-(4-chlorophenyl)butan-1-ol

4-(4-Chlorophenyl)-4-(methoxyimino)butanoic acid (Intermediate 15) (6.28 g, 26.00 mmol) in tetrahydrofuran (8 ml) was cooled, under an atmosphere of N2, in an ice-methanol bath then treated dropwise with borane-tetrahydrofuran complex (1.0M in THF) (26 ml, 26.00 mmol) over a period of 20 minutes. The resulting solution was allowed to warm to room temperature, stirred for 1 hour then heated at reflux for a further 6 hours. After cooling in ice-water the mixture was treated with water (6 ml) dropwise with stirring over 10 minutes. The mixture was again allowed to warm to room temperature and stirred for 2 hours before evaporating the bulk of the solvent. The residue was then cooled in ice-water and 50% NaOH(aq.) (6 ml) added dropwise with stirring. The resulting mixture was stirred and heated at 90° C. for 4 hours then cooled to room temperature and extracted with Et2O (3×). The combined extracts were washed with water followed by brine, dried over MgSO4 and evaporated to give 4-amino-4-(4-chlorophenyl)butan-1-ol (1.100 g, 21.2%) as a colourless, viscous oil which was used without further purification.

1. temperaturethen heated
2. temperatureat reflux for a further 6 hours
3. stirringwith stirring over 10 minutes
4. temperatureto warm to room temperature
5. stirringstirred for 2 hours
6. custombefore evaporating the bulk of the solvent
7. temperatureThe residue was then cooled in ice-water
8. addition50% NaOH(aq.) (6 ml) added dropwise
9. stirringwith stirring
10. stirringThe resulting mixture was stirred
11. temperatureheated at 90° C. for 4 hours
12. temperaturethen cooled to room temperature
13. extractionextracted with Et2O (3×)
14. washThe combined extracts were washed with water
15. dry with materialdried over MgSO4
16. customevaporated

ORD record

ord-c544e1abacfa431686a09c3c5a75129f

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101623B2