sodium tetrahydroborate; hydrogen; [Ni(O2CCH3)2]*4H2O in ethanol T=20°C; P=10343.2 Torr; 4 h; AutoclaveInert atmosphereLarge scale;

1: cis-cyclopentane-1,3-diol With (4S)-4-isopropyl-2-methoxy-3-((R)-2-methyl-1-(1-methyl-1H-imidazol-2-yl)propyl)oxazolidine; Pempidine hydrochloride in tetrahydrofuran T=20°C; 0.166667 h; Inert atmosphere; 2: tert-butyldimethylsilyl chloride With N-methyl-2,2,6,6-tetramethylpiperidine in tetrahydrofuran T=20°C; 4 h; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

(S)-N-((R)-3,3-dimethylbutan-2-yl)-3,3-dimethyl-2-(((1-methyl-1H-imidazol-2-yl)methyl)amino)butanamide; N-ethyl-N,N-diisopropylamine in tetrahydrofuran T=-78°C; 48 h; enantioselective reaction;

1: 53 percent / KH2PO4, H3PO4 / H2O / 40 h / 99 °C / pH 4.1 2: 72 percent / Et3N, DMAP / tetrahydrofuran / Ambient temperature 3: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C 4: H2 / Ni2B / methanol 5: 37 percent / Et3N, pancreatin / various solvent(s) / 27 h / Ambient temperature View Scheme

1: 72 percent / Et3N, DMAP / tetrahydrofuran / Ambient temperature 2: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C 3: H2 / Ni2B / methanol 4: 37 percent / Et3N, pancreatin / various solvent(s) / 27 h / Ambient temperature View Scheme

1: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C 2: H2 / Ni2B / methanol 3: 37 percent / Et3N, pancreatin / various solvent(s) / 27 h / Ambient temperature View Scheme

1: H2 / Ni2B / methanol 2: 37 percent / Et3N, pancreatin / various solvent(s) / 27 h / Ambient temperature View Scheme

Pancreatin; triethylamine in various solvent(s) 27 h; Ambient temperature;

1: lithium aluminium tetrahydride; lithium iodide / toluene; tert-butyl methyl ether / 3 h / -30 °C / |Inert atmosphere; |Large scale 2: triethylamine; Pancreatin / tert-butyl methyl ether / 7 h / |Inert atmosphere; |Large scale; |Enzymatic reaction 3: hydrogen; 5 Pt/Al2O3 View Scheme

1: triethylamine; Pancreatin / tert-butyl methyl ether / 7 h / |Inert atmosphere; |Large scale; |Enzymatic reaction 2: hydrogen; 5 Pt/Al2O3 View Scheme