Triethylamine → Benzyl (2-oxopyrrolidin-3-yl)carbamate

To a solution of 3-aminopyrrolidin-2-one (2.70 g, 27 mmol) in water (36 mL) at ambient temperature was added triethylamine (4.12 mL, 29.7 mmol, 1.1 equivalent) followed by the dropwise addition over 15 minutes of a solution of N-(benzyloxycarbonyloxy)succinimide (7.4 g, 29.7 mmol, 1.1 equivalent) in MeCN (20 mL). The mixture was stirred at room temperature for 22 hours. The mixture was evaporated and the residue was partitioned between 0.5 M aqueous NaOH (500 mL) and DCM (600 mL). The aqueous fraction was further extracted with DCM (2×250 mL) and the combined organic extracts were back-washed with water (300 mL), dried (MgSO4) and evaporated to a cream solid which was filtered, dried and evaporated then triturated with ether (50 mL) for 0.5 hours, before being dried at room temperature for 2 hours to give benzyl N-(2-oxopyrrolidin-3-yl)carbamate (D39) 4.4 g (70%);

1. customThe mixture was evaporated
2. customthe residue was partitioned between 0.5 M aqueous NaOH (500 mL) and DCM (600 mL)
3. extractionThe aqueous fraction was further extracted with DCM (2×250 mL)
4. washthe combined organic extracts were back-washed with water (300 mL)
5. dry with materialdried (MgSO4)
6. customevaporated to a cream solid which
7. filtrationwas filtered
8. customdried
9. customevaporated
10. customthen triturated with ether (50 mL) for 0.5 hours
11. custombefore being dried at room temperature for 2 hours

ORD record

ord-a56e09eff47c4713a53553d97c9366c1

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376436B2