HCID 131735574, compound → HCID 42606465, compound

Temperature

0 °C

2 g of the resulted N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]octadecyl-amide were transferred to a three necks round bottom flask equipped with a dropping funnel, a cooling bath, and a magnetic stirrer. The compound was dissolved in 50 ml dry THF and the solution was cooled to 0° C. 40 ml of 1.0 M solution of B2H6 in THF (borane tetrahydrofuran complex) were added dropwise through the dropping funnel during 2 hours and then the mixture was left to react for another 2 hours at 0° C. The cooling bath was removed and the reaction was left to stir overnight. The next day, 10 ml of H2O were added slowly and the solution was evaporated to dryness, transferred to a separatory funnel, and 100 ml water, 100 ml dichloromethane and 50 ml methanol were added. Following shaking, the lower phase was collected and the upper, aqueous-methanolic phase was extracted twice with 50 ml CH2Cl2:MeOH, 3:1. The combined organic phases were washed with 100 ml H2O, dried for 2 hours over MgSO4, filtered and the solution was evaporated to dryness. The resulted product was crystallized from ethanol:H2O. Yield: 0.9 g.

1. customequipped with a dropping funnel, a cooling bath, and a magnetic stirrer
2. waitthe mixture was left
3. customto react for another 2 hours at 0° C
4. customThe cooling bath was removed
5. waitthe reaction was left
6. additionThe next day, 10 ml of H2O were added slowly
7. customthe solution was evaporated to dryness
8. customtransferred to a separatory funnel
9. addition100 ml water, 100 ml dichloromethane and 50 ml methanol were added
10. stirringFollowing shaking
11. customthe lower phase was collected
12. extractionthe upper, aqueous-methanolic phase was extracted twice with 50 ml CH2Cl2
13. washThe combined organic phases were washed with 100 ml H2O
14. dry with materialdried for 2 hours over MgSO4
15. filtrationfiltered
16. customthe solution was evaporated to dryness
17. customThe resulted product was crystallized from ethanol

ORD record

ord-e9e2e2eff67e4f37afc080cee3da514c

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09340488B2