Acetic Acid → (S)-1-Boc-2-methyl-4-isopropylpiperazine

Participants

Role	Name	HCID	Charge
Reactant	Acetic Acid	HCID 176	—
Reactant	Acetone	HCID 180	—
Reactant	Sodium triacetoxyborohydride	HCID 5049666	—
Reactant	tert-Butyl (2R)-2-methylpiperazine-1-carboxylate	HCID 10262201	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(S)-1-Boc-2-methyl-4-isopropylpiperazine	HCID 86700418	—

Reaction Conditions

Temperature	60 °C

Reaction Steps

To (R)-1-Boc-2-methylpiperazine (200.0 mg, 0.999 mmol) and sodium triacetoxyborohydride (444.5 mg, 2.097 mmol) in DMF (5 mL) was added acetone (116 mg, 0.147 mL, 1.997 mmol) and acetic acid (90.0 mg, 86 μL, 1.498 mmol). The reaction mixture was heated at 60° C. for 1 h. The reaction mixture was diluted with water and extracted three times with diethyl ether. The combined organics were dried over sodium sulfate, filtered, concentrated, and used without further purification. LCMS-ESI+: calc'd for C13H27N2O2 (M+H+): 243.2; Found: 243.2 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987250B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-c742acede27c4fd587e8beaefcc08653
Source note	uspto-grants-2015_03