(R)-1-Boc-3-Hydroxypiperidine

White powder

(R)-1-Boc-3-hydroxypiperidine has been used as a reactant for the synthesis of piperidinyl and pyrrolidinyl butyrates. It has also been used for the synthesis of constrained (-)-S-adenosyl-L-homocysteine (SAH) analogs as DNA methyltransferase inhibitors.

A suspension of (3R)-piperidin-3-ol hydrochloride (3.17 g, 0.023 mol) in CH2Cl2 (40 mL) was treated with Na2CO3 (5.13 g, 0) dissolved in H2O (80 mL) 0.048 mol) and then treated with diiron dicarbonate/fluorobutyl ester (5.53 g, 0.025 mol) and additional CH2Cl3 (24 mL). The resulting mixture was stirred for 21 hours. The layers were separated and the aqueous phase was extracted with CH2Cl2 (3x50) mL) to extract the aqueous phase. The combined organic layers were dried with Na2SO4, filtered, and concentrated in vacuo. The residue was analyzed by column chromatography (9:1 CH2Cl2:MeOH) purification to give colorless oily (R)-1-Boc-3-hydroxypiperidine (5.07 g, quantitative). Mass spectrum (M+1): 202.0. 1H NMR (400 MHz, chloroform-D) ppm of 1.40-1.56 (M, 2h), 1.44 (s, 9h), 1.67-1.80 (M, 1H), 1.80-1.93 (M, 1 H), 2.95-3.22 (M, 2h), 3.47 (D, J=5.1 Hz, 1H), 3.51 (brs, 1H) and 3.64-3.78 (M, 2 H).