Phenol → HCID 66787677, compound

To the phenol T81-6(S) (1.4 g, 8.42 mmol, 1.0 eq) in DMF (16 mL) was added potassium carbonate (1.6 g, 8.42 mmol, 1 eq), and (R)-methylcarbonate (T81-A, 0.73 mL, 8.42 mmol, 1.0 eq). The resulting mixture was stirred at 85° C. for 72 h with monitoring of the reaction by TLC [(ethyl acetate/hexanes:2/8); Rf=0.30, UV, CMA]. The mixture was cooled to room temperature and brine was added. The aqueous phase was extracted with ethyl acetate and the combined organic phases were extracted with brine. The organic phase was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (ethyl acetate/hexanes, 2/8, Rf=0.30) to give T81-7(1R,8S) (1.45 g, 76%). Use of (S)-methylcarbonate in this reaction led to T81(1S,8S) containing a (1S)-stereocenter through the same transformations as described below for the corresponding (1R)-isomer.

1. extractionThe aqueous phase was extracted with ethyl acetate
2. extractionthe combined organic phases were extracted with brine
3. dry with materialThe organic phase was dried over MgSO4
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by flash chromatography (ethyl acetate/hexanes, 2/8, Rf=0.30)
6. customto give T81-7(1R,8S) (1.45 g, 76%)
7. additioncontaining a (1S)-stereocenter through the same transformations

ORD record

ord-c912066e739f40c5b0ac787c9bea7751

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133235B2