tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate → (S)-tert-Butyl 2-((1R,2S)-1-hydroxy-2-methylbut-3-en-1-yl)pyrrolidine-1-carboxylate

To a solution of tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate (10 g, 50 mmol, 1 eq.) in dichloromethane (120 mL, 0.42 M) was added potassium (2Z)-2-buten-1-yltrifluoroborate (9.76 g, 60.2 mmol, 1.2 eq.) followed by tetra-n-butylammonium bromide (3.24 g, 5.02 mmol, 0.1 eq.) and water (60 mL). After 13 hours, the reaction was diluted with dichloromethane (150 mL) and water (150 mL). The aqueous layer was separated and back-extracted with dichloromethane (100 mL). The combined organic layers were washed with aqueous sodium chloride solution (5% wt, 200 mL), washed with water (200 mL), and concentrated in vacuo to afford #9 (˜13 g) as an orange oil, which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 5.61-5.86 (br m, 1H), 4.97-5.09 (m, 2H), 3.80-3.98 (br m, 2H), 3.45-3.67 (br m, 1H), 3.21-3.29 (m, 1H), 2.14-2.26 (m, 1H), 1.80-2.04 (m, 3H), 1.65-1.76 (m, 1H), 1.47 (s, 9H), 1.12 (d, J=6.6 Hz, 3H).

1. customThe aqueous layer was separated
2. extractionback-extracted with dichloromethane (100 mL)
3. washThe combined organic layers were washed with aqueous sodium chloride solution (5% wt
4. wash200 mL), washed with water (200 mL)
5. concentrationconcentrated in vacuo

ORD record

ord-3f262d319c2749dfa937ad3296635aa7

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828401B2