Dichloromethane → Tert-butyl 3-(azidomethyl)-4-hydroxy-pyrrolidine-1-carboxylate

温度

0 °C

Ms-Cl (0.38 mL, 2.6 eq) was added to a solution of 3-hydroxy-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (mixture of stereoisomers, prepared according to WO9303026, 410 mg, 1.89 mmol) in pyridine (3.5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h. Then DCM was added and the mixture was washed with sat. aq. NaHCO3, dried over MgSO4, concentrated under reduced pressure and dried at HV. The crude mesylate was dissolved in DMF (18 mL), treated with NaN3 (1.23 g, 10 eq) and stirred at 95° C. for 1.5 h. After cooling to rt the mixture was concentrated to dryness and dissolved in DCM. The org. layer was washed with water, dried over MgSO4, concentrated under reduced pressure and the residue was purified by CC (DCM to DCM/MeOH 95:5) to afford the title intermediate as a yellow oil (390 mg, 85%).

1. washthe mixture was washed with sat. aq. NaHCO3
2. dry with materialdried over MgSO4
3. concentrationconcentrated under reduced pressure
4. customdried at HV
5. dissolutionThe crude mesylate was dissolved in DMF (18 mL)
6. stirringstirred at 95° C. for 1.5 h
7. temperatureAfter cooling to rt the mixture
8. concentrationwas concentrated to dryness
9. dissolutiondissolved in DCM
10. washlayer was washed with water
11. dry with materialdried over MgSO4
12. concentrationconcentrated under reduced pressure
13. customthe residue was purified by CC (DCM to DCM/MeOH 95:5)

ORDレコード

ord-8b45af036ea54f54b1e48d566a2083ee

出典データセット

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08217029B2