3-Oxo-1-oxa-8-aza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester Chemical Properties

Melting point:

65-66 °C(Solv: hexane (110-54-3))

Boiling point:

375.5±42.0 °C(Predicted)

Density 

1.16

storage temp. 

2-8°C

pka

-0.85±0.20(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C13H21NO4/c1-12(2,3)18-11(16)14-6-4-13(5-7-14)8-10(15)9-17-13/h4-9H2,1-3H3

InChIKey

XDSCHYPLQWGQRC-UHFFFAOYSA-N

SMILES

O1C2(CCN(C(OC(C)(C)C)=O)CC2)CC(=O)C1

3-Oxo-1-oxa-8-aza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester Usage And Synthesis

Uses

tert-Butyl 3-Oxo-1-oxa-8-azaspiro[4.5]decane-8-carboxylate is used as a reactant in organic synthesis.

Synthesis

General procedure for the synthesis of tert-butyl 3-oxo-1-oxa-8-azaspiro[4.5]decane-8-carboxylate from tert-butyl 3-hydroxy-1-oxa-8-azaspiro[4.5]decane-8-carboxylate: tert-butyl 3-hydroxy-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (30 g, 120 mmol) was dissolved at 0 °C in DMSO ( 300 mL) and triethylamine (58.5 mL, 420 mmol) was added. Subsequently, pyridine sulfur trioxide (65 g, 410 mmol, CAS No. 26412-87-3) was added in batches. The reaction mixture was stirred at room temperature for 2 h. The progress of the reaction was monitored by TLC (10% isopropanol/heptane) using iodine stain for color development. Upon completion of the reaction, the solution was poured into ice-cold water (1 L) and extracted with ethyl acetate (3 × 300 mL). The combined organic layers were washed sequentially with 0.5 N HCl (3 × 400 mL), sodium sulfite solution (1 × 400 mL), and saturated brine (1 × 400 mL). The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give about 33 g of an orange oil. The oily substance was purified by fast column chromatography (2-20% isopropanol/heptane) to afford tert-butyl 3-oxo-1-oxa-8-azaspiro[4.5]decane-8-carboxylate as a white solid (28.8 g, 97% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 1.44-1.52 (m, 9H), 1.61-1.73 (m, 2H), 1.75-1.87 (m, 2H), 2.38 (s, 2H), 3.40 (ddd, J = 13.48, 10.24, 3.24 Hz, 2H), 3.67 (dt, J = 13.57, 4.48 Hz, 2H), 4.04 (s, 2H).

References

[1] Patent: WO2010/58318, 2010, A1. Location in patent: Page/Page column 26-27
[2] Patent: WO2018/26371, 2018, A1. Location in patent: Paragraph 0320

3-Oxo-1-oxa-8-aza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester(954236-44-3)Related Product Information

• 1-Oxa-8-aza-spiro[4.5]decan-3-one
• 1-Oxa-8-azaspiro[4.5]decane
• 1,1-Dimethylethyl 1-oxa-8-azaspiro[4.5]decane-8-carboxylate
• 3-Oxo-1-oxa-8-aza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester