(S)-N-Boc-2-Hydroxymethylmorpholine

Bezeichnung:(S)-N-Boc-2-Hydroxymethylmorpholine

CAS-Nr135065-76-8

Englisch Name:(S)-N-Boc-2-Hydroxymethylmorpholine

CBNumberCB3958331

SummenformelC10H19NO4

Molgewicht217.26

MOL-Datei135065-76-8.mol

(S)-N-Boc-2-Hydroxymethylmorpholine physikalisch-chemischer Eigenschaften

Schmelzpunkt	60-62 °C
Siedepunkt	321 °C
Dichte	1.118
Flammpunkt	148 °C
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
Aggregatzustand	solid
pka	14.36±0.10(Predicted)
Farbe	White
Wasserlöslichkeit	Slightly soluble in water.
Sensitive	Light Sensitive
InChI	InChI=1S/C10H19NO4/c1-10(2,3)15-9(13)11-4-5-14-8(6-11)7-12/h8,12H,4-7H2,1-3H3/t8-/m0/s1
InChIKey	FJYBLMJHXRWDAQ-QMMMGPOBSA-N
SMILES	N1(C(OC(C)(C)C)=O)CCO[C@H](CO)C1
CAS Datenbank	135065-76-8

Sicherheit

HS Code

2933998090

Gefahreninformationscode (GHS)

(S)-N-Boc-2-Hydroxymethylmorpholine Chemische Eigenschaften,Einsatz,Produktion Methoden

Verwenden
(S)-N-Boc-2-hydroxymethylmorpholine is used as a pharmaceutical intermediate.
Synthese

911223-10-4

135065-76-8

Under stirring conditions, (S)-tert-butyl 2-((benzyloxy)methyl)morpholine-4-carboxylate (5.27 g, 17.2 mmol) was dissolved in 200 mL of ethanol, followed by the addition of 0.527 g of palladium/activated carbon catalyst and two drops of 1N hydrochloric acid. The reaction system was replaced three times with hydrogen and then reacted overnight at 70 °C under hydrogen atmosphere, and the reaction progress was monitored by thin layer chromatography (TLC) until the feedstock was completely consumed. Upon completion of the reaction, the reaction was quenched with 100 mL of saturated sodium bicarbonate solution and extracted with ethyl acetate (200 mL × 4). The organic phases were combined, washed sequentially with 100 mL of water and 100 mL of saturated saline, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford (S)-N-Boc-2-hydroxymethylmorpholine (3.646 g, 97.7% yield) as colorless to light yellow liquid. Mass spectrum (ESI) m/z: 240.3 [M + 23]. 1H NMR (CDCl3, 400 MHz) δ 3.92-3.88 (m, 3H), 3.7-3.64 (m, 1H), 3.60-3.48 (m, 3H), 2.936 (m, 1H), 2.75 (m, 1H), 2.06 (m, 1H), 1.46 (s , 9H).
Einzelnachweise
[1] Patent: EP2189451, 2010, A1. Location in patent: Page/Page column 14
[2] Patent: US2010/210640, 2010, A1. Location in patent: Page/Page column 13
[3] Patent: WO2007/6715, 2007, A1. Location in patent: Page/Page column 34; 35
[4] Patent: WO2007/6714, 2007, A1. Location in patent: Page/Page column 122
[5] Patent: WO2006/105262, 2006, A1. Location in patent: Page/Page column 74; 75

(S)-N-Boc-2-Hydroxymethylmorpholine Upstream-Materialien And Downstream Produkte

(S)-N-Boc-2-Hydroxymethylmorpholine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

135065-76-8, (S)-N-Boc-2-Hydroxymethylmorpholine Verwandte Suche:

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