Hydrochloric Acid → HCID 66934433, compound

Temperature

80 °C

The product of step (d) (mixture of diastereomers, 234 mg, 1.54 mmol) was dissolved in 5 mL EtOH and treated with NaBH4 (117 mg, 3.1 mmol). After stirring for 15 minutes, the reaction was quenched with HOAc and diluted with water (10 mL). The product was extracted into DCM (2×25 mL) and the extracts were concentrated to dryness. The crude residue was dissolved in HOAc (8 mL) and concentrated HCl (4 mL) and treated with SnCl2 (1.4 g, 6.2 mmol). After heated to 80° C. for 1 hour, the reaction was cooled and diluted with water (15 mL). The product was extracted into DCM (3×25 mL) and the extracts were dried over MgSO4 and concentrated to dryness. The diastereomers were separated by HPLC (Novapak C-18, 19×300 mm, 55% CH3CN/water, 10 mL/min) to give diastereomer 1 (rt=23.0 min) and diastereomer 2 (rt=24.2 min) giving approximately 20 mg of each diastereomer.

1. customthe reaction was quenched with HOAc
2. additiondiluted with water (10 mL)
3. extractionThe product was extracted into DCM (2×25 mL)
4. concentrationthe extracts were concentrated to dryness
5. dissolutionThe crude residue was dissolved in HOAc (8 mL)
6. temperaturethe reaction was cooled
7. extractionThe product was extracted into DCM (3×25 mL)
8. dry with materialthe extracts were dried over MgSO4
9. concentrationconcentrated to dryness
10. customThe diastereomers were separated by HPLC (Novapak C-18, 19×300 mm, 55% CH3CN/water, 10 mL/min)
11. customto give diastereomer 1 (rt=23.0 min) and diastereomer 2 (rt=24.2 min)
12. customgiving approximately 20 mg of each diastereomer

ORD record

ord-1f0315782272434da03f3dbecc8fcde6

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07893051B2