Triethylamine → 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

2-tert-Butoxycarbonyloxyimino-2-phenylacetonitrile (1.25 g.) was added to a solution of L-proline (575 mg.) and triethylamine (0.7 ml.) in a mixture of methanol (7.5 ml.), dioxane (2.5 ml.) and water (5.0 ml.) at room temperature. The reaction mixture was concentrated under reduced pressure and benzene and water were added to the residue. After shaking the resultant mixture, the aqueous layer was separated from the mixture, washed with benzene, acidified with hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated. A mixture of ether and n-hexane was added to the residue and the residue was added a mixture of ether and n-hexane and the precipitated crystals were collected by filtration and dried to give N-tert-butoxycarbonyl-L-proline (845 mg.), mp (845 mg.), mp 133° to 134° C.

1. concentrationThe reaction mixture was concentrated under reduced pressure and benzene and water
2. additionwere added to the residue
3. customthe aqueous layer was separated from the mixture
4. washwashed with benzene
5. extractionextracted with ethyl acetate
6. washThe extract was washed with water
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated
9. additionA mixture of ether and n-hexane
10. additionwas added to the residue
11. additionthe residue was added
12. additiona mixture of ether and n-hexane
13. filtrationthe precipitated crystals were collected by filtration
14. customdried

ORD record

ord-d51181f658c4450e95b9b4ebfc6d80ab

Source dataset

uspto-grants-1977_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04014915