Triethylamine → HCID 58210349, compound

Temperature

50 °C

Acetic acid 5-acetoxy-6-oxo-tetrahydro-pyran-2-ylmethyl ester (2.3) (2.30 g, 10.0 mmol) was dissolved in ethyl acetate (50 mL) and added to the Parr reactor, followed by Pd/C (5%, 0.2 g) and triethylamine (4.3 mL, 30.0 mmol). The mixture was stirred under hydrogen (5×106 Pa) and heated at 50° C. for 1 day. The product was filtered through celite and the solvent removed under vacuum. The crude product was dissolved in CH2Cl2 (200 mL) and washed with water (3×200 mL). The solvent was removed and the resulting product dried under vacuum. The resulting syrup was sublimed under vacuum, at 50° C., affording white crystals (1.20 g, 7.0 mmol, 70%). 1H NMR (400 MHz, CDCl3) δ 5.46 (1H, dd, 3JH—H=10.56 Hz, 3JH—H=8.87 Hz, H-2), 4.60 (1H, m, H-5), 2.36 (1H, m, H-3), 2.20 (3H, s, COCH3), 2.12-2.00 (1H, m, H-4), 2.00-1.88 (1H, m, H-3′), 1.88-1.75 (1H, m, H-4′), 1.42 (3H, d, 3JH—H=6.22 Hz, H-6) ppm. 13C {1H} NMR (125 MHz, CDCl3) δ 169.9, 169.6 (COCH3, C-1), 74.2 (C-5), 66.0 (C-2), 27.8 (C-4), 23.0 (C-3), 21.0 (C-6), 20.8 (COCH3) ppm. m/z (CI-ammonia gas): 190 [M+NH4+]. Anal. Calcd for C8H12O4: C, 55.81; H, 7.02. Found: C, 55.81; H, 7.05.

1. additionadded to the Parr reactor
2. filtrationThe product was filtered through celite
3. customthe solvent removed under vacuum
4. dissolutionThe crude product was dissolved in CH2Cl2 (200 mL)
5. washwashed with water (3×200 mL)
6. customThe solvent was removed
7. customthe resulting product dried under vacuum
8. customwas sublimed under vacuum, at 50° C.

ORD record

ord-df6ec974c43d4d10bbf4eb4fc15a4f39

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476402B2