Triethylamine → HCID 69748793, Verbindung

In a flask (3R,4R)-4-benzyloxycarbonylamino-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (3.93 g, 10.4 mmol) was dissolved in dichloromethane (200 mL) and then benzotriazol-1-yloxy-tripyrrolidinophosphonium hexafluorophosphate (6.48 g, 12.5 mmol) and triethylamine (3.3 mL, 23.7 mmol) were added. After stirring for 5 minutes, (S)-3-(4-fluorobenzyl)-piperidine (2.21 g, 11.4 mmol) was added. The mixture was stirred for 16 hours. The reaction mixture was extracted with water (50 mL) and brine (50 mL). The organic layer was dried with magnesium sulfate, filtered, and concentrated in vacuo to give a crude orange glass (10.49 g). Purification by flash column chromatography (50-70% ethyl acetate/hexanes) provided a colorless oil (4.79 g, 83%). 1H NMR (300 MHz, CDCl3), δ: 7.32 (m, 2H), 7.26 (m, 3H), 7.07 (m, 2H), 6.95 (m, 2H), 5.04 (m, 2H), 4.41 (d, 1H, J=13), 4.12 (bm, 2H), 3.83 (bm, 2H), 3.06 (bm, 1H), 2.76 (bs, 2H), 2.60 (dd, 2H, J=14, J′=6), 2.37 (m, 2H), 1.90 (bs, 1H), 1.63 (bm, 2H), 1.45 (m, 9H), 1.12 (m, 3H), 0.87 (m, 1H).

1. stirringThe mixture was stirred for 16 hours
2. extractionThe reaction mixture was extracted with water (50 mL) and brine (50 mL)
3. dry with materialThe organic layer was dried with magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto give a crude orange glass (10.49 g)
7. customPurification by flash column chromatography (50-70% ethyl acetate/hexanes)

ORD-Eintrag

ord-bb57bd7aa72d41e098f328a61ba16332

Quelldatensatz

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06949546B2