Triethylamine → tert-Butyl 1-((benzo[b]thiophen-5-yloxy)methyl)pyrrolidine-2-carboxylate

Temperature

0 °C

Polymer supported triphenyl phosphine (5.12 g, 13.32 mmol, 2.6 mmol/g loading) was suspended in dichloromethane (15 mL) cooled to 0° C. in an ice/water bath. Diisopropyl azodicarboxylate (2.69 g, 13.3 mmol, 2.6 mL) was added dropwise and the mixture was stirred for 10 min. A solution of benzo[b]thiophen-5-ol (1.20 g, 7.99 mmol) and (S)-tert-butyl-2-(hydroxymethyl)pyrrolidine-1-carboxylate (1.34 g, 6.66 mmol) dissolved in dichloromethane (20 mL) was added dropwise at 0° C. The cooling bath was removed, triethylamine (1.35 g, 13.3 mmol) was added, and the mixture was stirred for 16 h. The polymer bound triphenylphosphine was removed by filtration and washed with dichloromethane (3×10 mL). The organic layer was separated, dried over sodium sulfate (200 mg), filtered through a coarse frit (to remove the sodium sulfate), and condensed in vacuo to give a white solid (2.3 g). The crude product was purified by flash chromatography (EtOAc/hexane 1:1) to yield the title compound as a white solid (1.95 g, 55%). MS (M+H)+ 334.

1. additionwas added dropwise at 0° C
2. customThe cooling bath was removed
3. stirringthe mixture was stirred for 16 h
4. customwas removed by filtration
5. washwashed with dichloromethane (3×10 mL)
6. customThe organic layer was separated
7. dry with materialdried over sodium sulfate (200 mg)
8. filtrationfiltered through a coarse frit (
9. customto remove the sodium sulfate), and
10. customcondensed in vacuo

ORD record

ord-5f14406bc8ec49d19b6badb6c5990ddb

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858785B2