Lithium aluminum hydride → HCID 86717506, compound

Temperature

0 °C

Methyl (1S,2R,4S)-4-[(tert-butoxycarbonyl)amino]-2-methoxycyclohexanecarboxylate (racemic) (0.87 g, 3.0 mmol) were dissolved in ether (27 mL) and cooled to 0° C. Lithium tetrahydroaluminate (138 mg, 3.63 mmol) was added and the resulting reaction mixture was stirred for 4 h. The reaction was quenched with 5 mL water at 0° C., then diluted with 5 mL 15% NaOH and 15 mL water after stirring for 30 min. The reaction mixture was filtered through a pad of Celite and washed with ethyl acetate. The aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The crude was purified with flash chromatography (eluting with a gradient of 0-80% ethyl acetate in hexanes) to give the desired product as white foam.

1. customthe resulting reaction mixture
2. customThe reaction was quenched with 5 mL water at 0° C.
3. additiondiluted with 5 mL 15% NaOH and 15 mL water
4. stirringafter stirring for 30 min
5. filtrationThe reaction mixture was filtered through a pad of Celite
6. washwashed with ethyl acetate
7. extractionThe aqueous layer was extracted with ethyl acetate (2×)
8. washThe combined organic layers were washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customThe crude was purified with flash chromatography (
13. washeluting with a gradient of 0-80% ethyl acetate in hexanes)

ORD record

ord-87b633e710814378a26be54a1522324d

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181271B2