Methyl iodide → 3-(Methylamino)propanoic acid, N-BOC protected

60% NaH in mineral oil (0.528 g, 13.21 mmol) was washed with hexane (2×10 mL). It was suspended in dry THF (6 mL) and cooled to 0° C. before BOC-BETA-ALA-OH (1 g, 5.29 mmol) in dry THF (6 mL) was added. MeI (0.823 mL, 13.21 mmol) in dry THF (6 mL) was dropwise added after 5 min. and the resulting suspension was stirred at 0° C. to room temperature over the weekend. The reaction mixture was quenched with ice cold H2O (50 mL) and washed with Et2O (25 mL). The aqueous layer was acidified with concentrated aqueous HCl (3 mL) and extracted with EtOAc (3×20 mL). The combined EtOAc extracts were dried (Na2SO4) and concentrated to afford the desired product (1.095 g, quantitative) as a yellow oil.

1. additionwas added
2. customThe reaction mixture was quenched with ice cold H2O (50 mL)
3. washwashed with Et2O (25 mL)
4. extractionextracted with EtOAc (3×20 mL)
5. dry with materialThe combined EtOAc extracts were dried (Na2SO4)
6. concentrationconcentrated

ORD record

ord-64364645bbf74290b8820894ebafcdaa

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302988B2