Benzyl chloroformate → Benzyl ((S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)carbamate

To a solution of (5)-2-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-1-ol (50 g, 312.5 mmol) and K2CO3 (129.375 g, 937.5 mmol) in dioxane (250 mL) and water (250 mL) at 0° C. was added CbzCl (106.6 g, 625 mmol) dropwise. The reaction mixture was stirred at room temperature until the staring material disappeared. The organic solvent was distilled and the residue was dissolved in AcOEt (200 mL). The organic phase was separated and the water was extracted with AcOEt (3×100 ml). The combined organic phase was washed with water (3×50 ml), dried over Na2SO4, and concentrated in vacuo to give the residue, which was purified by column to give the product (26 g). 1H NMR (CD3OD) 1.1-1.3 (m, 2H), 1.4-1.5 (m, 1H), 1.5-1.7 (m, 3H), 1.8-1.9 (m, 1H), 2.6-2.8 (m, 1H), 3.0-3.1 (t, 1H), 3.3-3.4 (m, 1H), 3.5-3.6 (m, 1H), 3.6-3.8 (m, 2H), 3.8-3.9 (m, 2H), 5.0-5.1 (s, 2H), 7.3-7.4 (m, 5H).

1. distillationThe organic solvent was distilled
2. dissolutionthe residue was dissolved in AcOEt (200 mL)
3. customThe organic phase was separated
4. extractionthe water was extracted with AcOEt (3×100 ml)
5. washThe combined organic phase was washed with water (3×50 ml)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. customto give the residue, which
9. customwas purified by column

ORD record

ord-41dd1541c36b404fae1b92b7e9d2d9a0

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106221B2