Water → HCID 86584164, compound

Temperature

0 °C

To a 12 L 3-neck round bottom flask was added isopropyl acetate (6.5 L). The solvent was cooled to 0° C. in an ice-water bath and 3-amino-1-propanol (1.14 Kg, 15.1 mol, 2.15 eq) was added in one portion. To this rapidly stirring solution, benzyl chloroformate (1.20 Kg, 7.03 mol, 1.0 eq) was added dropwise over 2h while maintaining the internal temperature of the flask between 10° C. and 15° C. After the addition was complete, the reaction mixture was allowed to stir between 10° C. and 15° C. for an additional 0.3 h after which time water (3.5 L) was added in one portion. The solution was then partitioned and washed with an additional 2×3.5 L of water. The organic layer was dried over potassium carbonate and concentrated to give a solid that was dissolved in excess isopropyl acetate and precipitated from solution by adding the compound to heptane. The solid was filtered under nitrogen to yield 1.20 Kg (82%) of the desired product as a colorless solid.

1. temperaturewhile maintaining the internal temperature of the flask between 10° C. and 15° C
2. additionAfter the addition
3. additionwas added in one portion
4. customThe solution was then partitioned
5. washwashed with an additional 2×3.5 L of water
6. dry with materialThe organic layer was dried over potassium carbonate
7. concentrationconcentrated
8. customto give a solid
9. customprecipitated from solution
10. additionby adding the compound to heptane
11. filtrationThe solid was filtered under nitrogen

ORD record

ord-73d00be1513f4fbcb04f4de2c58b67e6

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313296B1