ChemicalBook CAS DataBase List (S)-3-Amino-1-N-Boc-piperidine

(S)-3-Amino-1-N-Boc-piperidine synthesis

9synthesis methods

Product Name:(S)-3-Amino-1-N-Boc-piperidine
CAS Number:625471-18-3
Molecular formula:C10H20N2O2
Molecular Weight:200.28

98977-36-7 Synthesis

98977-36-7
427 suppliers
$6.00/1g

625471-18-3
286 suppliers
$14.14/1gm:

Yield:625471-18-3 99%

Reaction Conditions:

with pyridoxal 5'-phosphate;isopropylamine in dimethyl sulfoxide; pH=7.5 at 50; for 50 h;Enzymatic reaction;enantioselective reaction;Reagent/catalyst;Temperature;

Steps:

General procedure for the transamination reaction with immobilized enzymes
General procedure: In a similar manner as previously described in [14], to 5 mL of a triethanolamine buffer (100 mM, pH 7.5) containing isopropylamine(1.1 M), TA-IMB enzyme (200 mg) and PLP (1.4 mM) were added. The mixture was stirred at 35 °C and 550 rpm for 5 minutes, and then a preheated solution (35 °C) of 1-Boc-3-piperidone (1, 0.26 mmol, 45 mM) in DMSO (750 μL,13% v/v) was added. The reaction was stirred at 35 °C and 550 rpm in an open vessel for 24 hours. The reaction was monitored by HPLC analysis and by TLC. At the end of the reaction, the enzyme was filtered under vacuum and washed with triethanolamine buffer (100 mM, pH 7.5, 3 × 2 mL). The recovered enzyme was suspended in buffer and stored at 4 °C. HCl (4 M) was added to the reaction mixture to reach pH 2 and the aqueous layer was extracted with CH2Cl2 (2 × 5 mL) to remove any starting material. After that, the pH of the solution was changed to pH 13 by addition of KOH and the aqueous layer extracted with CH2Cl2 (4 × 5 mL). The combined organic extracts were dried over Na2SO4, filtered and then evaporated under reduced pressure to yield 3-amino-1-Boc-piperidine (2). Each of the crude reaction mixtures were analyzed by NMR and HPLC.

References:

Petri, Antonella;Colonna, Valeria;Piccolo, Oreste [Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 60 - 66]

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