N-(tert-Butoxycarbonyl)-L-cysteine methyl ester → Boc-Cysteinol

A solution of methyl N-(tert-butoxycarbonyl)-L-cysteinate (2.6 g, 11.0 mmol) in THF (10 ml) stirred at 0° C. under N2 was treated with slow addition of a 1M solution of LiAlH4 in THF (20 mL, 20 mmol). The reaction mixture was slowly warmed up to room temperature and further stirred for 2 h, cooled to 0° C. and quenched with slow addition of water, then poured on a 15% solution of K2CO3 in water (25 mL), shaken well and extracted with DCM (3×100 mL), the organic layers were combined and dried over MgSO4, filtered and concentrated to afford the title compound as colorless oil, kept under N2 atmosphere all the times and used fresh without further purification. Assumed quantitative yield. MS: m/z=230.1 (MNa+).

1. temperaturecooled to 0° C.
2. customquenched with slow addition of water
3. additionpoured on a 15% solution of K2CO3 in water (25 mL)
4. stirringshaken well
5. extractionextracted with DCM (3×100 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-45c185afecf944238ed7d5420c09a384

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187415B2