4-Methylmorpholine → tert-Butyl (1,1,1-trifluoro-3-hydroxypropan-2-yl)carbamate

온도

0 °C

To a stirred solution of 338 (294 mg, 1.209 mmol) in THF (10 mL) at 0° C. under nitrogen was added sequentially NMM (159.5 μL, 1.451 mmol) neat via syringe and ethyl chloroformate (138.7 μL, 1.451 mmol) neat by syringe. After 45 min the resulting suspension was filtered through GF/F filter paper with THF and the filtrate was isolated and stirred at 0° C. under nitrogen. A solution of NaBH4 (45.74 mg, 1.209 mmol) in H2O (2 mL) was added and the cooling bath was removed. After about 15 min, the reaction was concentrated and the residue was resuspended in Et2O (30 mL) and H2O (30 mL) with stirring. After stirring for 5 min the layers were separated and the organic phase washed brine (1×30 mL). The organic phase was (MgSO4), filtered and concentrated to afford 240 mg (86%) of tert-butyl 1,1,1-trifluoro-3-hydroxypropan-2-ylcarbamate (340) as a white solid.

1. filtrationAfter 45 min the resulting suspension was filtered through GF/F
2. filtrationfilter paper with THF
3. customthe filtrate was isolated
4. customthe cooling bath was removed
5. concentrationthe reaction was concentrated
6. stirringH2O (30 mL) with stirring
7. stirringAfter stirring for 5 min the layers
8. customwere separated
9. washthe organic phase washed brine (1×30 mL)
10. filtrationfiltered
11. concentrationconcentrated

ORD 기록

ord-4022dc21ce12448e8d9401e7f10024dd

출처 데이터셋

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09133187B2