Step 4: Synthesis of 4-amino-1-methylcyclohexanol
4-(Benzylamino)-1-methylcyclohexanol (4.9 g, 22.3 mmol) was dissolved in methanol (150 mL) and 7% Pd/C (700 mg) was added at 7 °C. The reaction was carried out overnight under hydrogen atmosphere. Upon completion of the reaction, the mixture was filtered to remove the Pd/C catalyst, and the filtrate was concentrated under vacuum to give a white solid product, 4-amino-1-methylcyclohexanol (2.9 g, quantitative yield), which could be used directly in the subsequent steps without further purification.
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[2] Patent: US2015/158879, 2015, A1. Location in patent: Paragraph 0443; 0444
[3] Patent: US2016/200741, 2016, A1. Location in patent: Paragraph 0444-0445
[4] Patent: WO2011/139107, 2011, A2. Location in patent: Page/Page column 108-109