Water → (1R)-2-Chloro-1-(pyridin-3-yl)ethan-1-ol

Temperature

-25 °C

To a stirred solution of 3.67 g (11.5 mmol) of (-)-B-chlorodiisopinocampheylborane [(-)-DIP-C1]in 11 mL of THF at -25° C. was added a slurry of 1.00 g (5.21 mmol) of the product from Example 14 in 5 mL of THF via a cannula. Following the addition of 0.80 mL (5.79 mmol) of triethylamine, the reaction mixture was stirred at -25° C. for 4 days. To the mixture was added 10 mL of water which was then allowed to warm to room temperature. To the mixture was added 20 mL of ethyl acetate and the organic phase separated. The aqueous phase was neutralized with saturated NaHCO3 solution then extracted six times with ethyl acetate. The combined organic phase was concentrated in vacuo to afford a yellow oil. Hash chromatography (silica gel, 75-100% ethyl acetate-hexanes) afforded 561 mg (68%) of the title compound as a pale yellow oil: 1H NMR (400 MHz, CD3OD) δ5 8.58 (d, 1H, J=1.8 Hz), 8.46 (dd, 1H, J =4.9, 1.5 Hz), 7.90 (d, 1H, J=7.9 Hz), 7.44 (dd, 1H, J=7.9, 4.9 Hz), 4.93 (m, 1H), 3.75 (m, 2H).

1. temperatureto warm to room temperature
2. customthe organic phase separated
3. extractionthen extracted six times with ethyl acetate
4. concentrationThe combined organic phase was concentrated in vacuo
5. customto afford a yellow oil

ORD record

ord-5f0fc4fcec4e4c9e932771d83e9ad466

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05561142