3,3-Dimethylbutanal → HCID 69062615, compound

Temperature

25 °C

cis-2-Amino-cyclooctanecarboxylic acid methyl ester hydrochloride (0.25 g, 1.35 mmol) was dissolved in methanol (10 mL). Sodium acetate (0.22 g, 2.70 mmol) was added followed by 4 Å powdered molecular sieves (0.20 g) and 3,3-dimethyl-butyraldehyde (0.17 mL, 1.35 mmol). Sodium cyanoborohydride (0.17 g, 2.70 mmol) was added and the mixture was stirred at 25° C. for 16 h. The mixture was poured into a mixture of saturated aqueous sodium bicarbonate solution (20 mL) and ethyl acetate (30 mL). After shaking, both layers were passed through a plug of Celite. The organic layer was further washed with saturated aqueous sodium bicarbonate solution (10 mL), saturated aqueous brine solution (10 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the crude product, cis-2-(3,3-dimethyl-butylamino)-cyclooctanecarboxylic acid methyl ester (0.34 g, 1.26 mmol, 93%), as a clear oil. LC-MS (ESI) calcd for C16H31NO2 269.42, found [M+H+].

1. stirringAfter shaking
2. washThe organic layer was further washed with saturated aqueous sodium bicarbonate solution (10 mL), saturated aqueous brine solution (10 mL)
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo

ORD record

ord-dad91622320848e0acfd28a10741e6e5

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582626B2