ChemicalBook CAS DataBase List (R)-N-Boc-2-Hydroxymethylmorpholine

(R)-N-Boc-2-Hydroxymethylmorpholine synthesis

8synthesis methods

Product Name:(R)-N-Boc-2-Hydroxymethylmorpholine
CAS Number:135065-71-3
Molecular formula:C10H19NO4
Molecular Weight:217.26

(R)-N-Boc-2-hydroxymethylmorpholine was used to prepare Checkpoint kinase 1 by template screening. It was synthesized from ((R)-morpholin-2-yl)methanol and Di-tert-butyl dicarbonate under triethylamine basic conditions was stirred for 16 h at room temperature to give (R)-N-Boc-2 -Hydroxymethylmorpholine as a colourless oil， yield 64%.

(R)-tert-butyl 2-((benzyloxy)methyl)morpholine-4-carboxylate

135097-68-6
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135065-71-3
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Yield:135065-71-3 100%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen for 16 h;

Steps:

112 tert-butyl (2R)-2-(hydroxymethyl)morpholine-4-carboxylate
Intermediate 111 (19.8 g, 64.4 mmol) was stirred under an atmosphere of hydrogenin the presence of 10% Pd/C (1.98 g, 1.86 mmol) for 16 h. The catalyst wasremoved by vacuum filtration and the filtrate concentrated at reduced pressure to give 13.98 g (100% yield) of the title compound as a colourless viscous oil, which crystallised on standing.1H NMR (250 MHz, chloroform-d): 6 [ppm] 3.98 - 3.75 (m, 3H), 3.73 - 3.41 (m, 4H),3.03- 2.83 (m, 1H), 2.82-2.65 (m, 1H), 2.12 (t, J = 5.9 Hz, 1H), 1.45 (5, 9H).

References:

EVOTEC AG;DAVENPORT, Adam James;BRAEUER, Nico;FISCHER, Oliver Martin;ROTGERI, Andrea;ROTTMANN, Antje;NEAGOE, Ioana;NAGEL, Jens;GODINHO-COELHO, Anne-Marie WO2016/91776, 2016, A1 Location in patent:Page/Page column 290

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24424-99-5 Synthesis