Hydrochloric Acid → 1046832-12-5

To a cooled (0-5° C.) mixture of 11 (10.00 g, 41.44 mmol) and water (47 mL) was added 7 N aqueous HCl (47 ml, 331.50 mmol). Cooling bath was then removed and the reaction mixture was stirred at RT overnight. Then, the reaction mixture was basified to pH 9 by dropwise addition of 50% aqueous NaOH while maintaining the internal temperature <35° C. with an ice bath. The mixture was extracted with EtOAc (2×73 mL) followed by CH2Cl2 (2×71 mL). The organic extracts were dried (MgSO4) filtered and concentrated in vacuo to give a white residue that was recrystallised from CH2Cl2/hexane to afford (VII-n) (6.75 g, 83%) as a white crystalline solid; 1H NMR (400 MHz, CDCl3) δ 0.99 (s, 3H), 1.61 (td, J=13.9, 4.3 Hz, 2H), 2.09-2.19 (m, 4H), 2.55-2.65 (m, 6H), 3.74 (t, J=4.6 Hz, 4H).

1. temperatureTo a cooled
2. temperatureCooling bath
3. customwas then removed
4. additionThen, the reaction mixture was basified to pH 9 by dropwise addition of 50% aqueous NaOH
5. temperaturewhile maintaining the internal temperature <35° C. with an ice bath
6. extractionThe mixture was extracted with EtOAc (2×73 mL)
7. dry with materialThe organic extracts were dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a white residue that
11. customwas recrystallised from CH2Cl2/hexane
12. customto afford (VII-n) (6.75 g, 83%) as a white crystalline solid

ORD record

ord-6dcc5c26cb78437b84e610dd8b8c84bc

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178552B2