Lithium borohydride → Benzyl (3S*,4R*)-1-(tert-butoxycarbonyl)-4-formylpyrrolidin-3-ylcarbamate

To a solution of benzyl (3S*,4R*)-1-(tert-butoxycarbonyl)-4-(ethoxycarbonyl)pyrrolidin-3-ylcarbamate (4.4 g, 11.2 mmol) in 150 mL THF, LiBH4 (0.74 g, 33.6 mmol) was added and the mixture was stirred at 80° C. for 1.5 hours. The mixture was quenched with H2O, extracted with EtOAc, the combined organic extracts were dried with Na2SO4 and evaporated. The residue was re-dissolved in 300 mL CH2Cl2, activated MnO2 (3.86 g, 56 mmol) was added and the mixture was stirred for 24 hours at room temperature. MnO2 was filtered off through Celite, and the filtrate was evaporated giving the title aldehyde.

1. customThe mixture was quenched with H2O
2. extractionextracted with EtOAc
3. dry with materialthe combined organic extracts were dried with Na2SO4
4. customevaporated
5. dissolutionThe residue was re-dissolved in 300 mL CH2Cl2
6. stirringthe mixture was stirred for 24 hours at room temperature
7. filtrationMnO2 was filtered off through Celite
8. customthe filtrate was evaporated

ORDレコード

ord-0577f149cd0344748dc03bd68d7b010d

出典データセット

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08497383B2