Methanesulfonyl chloride → 3-((Tert-butoxycarbonyl)amino)propyl methanesulfonate

Temperature

0 °C

To a solution of 3-(Bocamino)-1-propanol (10.51 g: 60 mmol) and TEA (6.07 g; 60 mmol) in dry DCM (100 mL) kept in an ice bath (0° C.) was slowly added methane sulfonyl chloride (6.87 g; 60 mmol) and the reaction mixture was stirred for 30 min at 0° C. The ice bath was removed and the reaction mixture was allowed to stir at room temperature for 5 h (completion of the reaction was monitored by TLC). Water (50 mL) was added with stirring and the resulting mixture was transferred to a reparatory funnel, the layers were separated, and the aqueous layer was extracted with DCM (2×75 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate, and concentrated to yield compound 5 as a colorless oil (12.82 g: 100% yield). 1H NMR (CDCl3) δ 4.8 (s, 1H), 4.3 (m, 1H), 3.3 (m, 2H), 3.2 (m, 2H), 1.9 (m, 2H), 1.4 (s, 9H).

1. custom(0° C.)
2. customThe ice bath was removed
3. stirringto stir at room temperature for 5 h (completion of the reaction
4. additionWater (50 mL) was added
5. stirringwith stirring
6. customthe resulting mixture was transferred to a reparatory funnel
7. customthe layers were separated
8. extractionthe aqueous layer was extracted with DCM (2×75 mL)
9. washThe combined organic layers were washed with brine (50 mL)
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated

ORD record

ord-a303b9a89e9947f3baad5283e080453c

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309284B2