1-OXA-6-AZASPIRO[2.5]OCTANE-6-CARBOXYLIC ACID, 1,1-DIMETHYLETHYL ESTER Chemical Properties

Melting point:

50-52℃

Boiling point:

297.6±33.0 °C(Predicted)

Density 

1.12

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-0.82±0.20(Predicted)

form 

Crystalline Powder

color 

White

InChI

InChI=1S/C11H19NO3/c1-10(2,3)15-9(13)12-6-4-11(5-7-12)8-14-11/h4-8H2,1-3H3

InChIKey

ULSBMKGFFFMGOI-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-26-36/37/39-45

HazardClass 

IRRITANT

HS Code 

29349990

1-OXA-6-AZASPIRO[2.5]OCTANE-6-CARBOXYLIC ACID, 1,1-DIMETHYLETHYL ESTER Usage And Synthesis

Uses

1-Oxa-6-azaspiro[2.5]octane-6-carboxylic Acid tert-Butyl Ester is used in the synthesis of a T-type Ca2+ channel antagonist, 4-Aminomethyl-4-fluoropiperidine.

Synthesis

General procedure for the synthesis of tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate from N-tert-butoxycarbonyl-4-piperidone: [Reference Example 1] Synthesis of tert-butyl 6-azaspiro[2.5]octane-6-carboxylate. 60% NaH-oil packet (5.28 g, 132 mmol) was suspended in dimethylsulfoxide (DMSO) (250 mL) and after cooling to 0°C, trimethylsulfonium iodide (29.0 g, 132 mmol) was added. The reaction mixture was warmed to room temperature and stirred for 40 min. Subsequently, N-Boc-4-piperidone (Boc = tert-butoxycarbonyl) (25.0 g, 125 mmol) was added and the reaction mixture was stirred at room temperature for 1 hr and then at 55 °C for 1.5 hrs. After completion of the reaction, the mixture was poured into ice-cooled water (500 mL) and extracted with ethyl acetate (AcOEt) (500 mL × 3 times). The ethyl acetate layers were combined, washed with water, then with saturated brine and finally dried with anhydrous Na2SO4. After filtration, the filtrate was concentrated to give tert-butyl 6-aza-1-oxaspiro[2.5]octane-6-carboxylate. The product was structurally confirmed by 1H-NMR. The yield was 26.4 g (99%).1H-NMR (270 MHz, CDCl3): δ 1.40-1.49 (m, 2H), 1.46 (s, 9H), 1.74-1.85 (m, 2H), 2.69 (s, 2H), 3.37-3.48 (m, 2H), 3.68-3.77 (m, 2H).

References

[1] Patent: EP1505067, 2005, A1. Location in patent: Page/Page column 368
[2] Patent: WO2008/10765, 2008, A1. Location in patent: Page/Page column 66-67
[3] Patent: US2010/4239, 2010, A1. Location in patent: Page/Page column 93
[4] Patent: WO2005/49620, 2005, A1. Location in patent: Page/Page column 24
[5] Patent: CN108727400, 2018, A. Location in patent: Paragraph 0115; 0118; 0120

1-OXA-6-AZASPIRO[2.5]OCTANE-6-CARBOXYLIC ACID, 1,1-DIMETHYLETHYL ESTER(147804-30-6)Related Product Information

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• 1-OXA-5-AZASPIRO[2.5]OCTANE-5-CARBOXYLIC ACID, 1,1-DIMETHYLETHYL ESTER
• 1-OXA-6-AZASPIRO[2.5]OCTANE-6-CARBOXYLIC ACID, 1,1-DIMETHYLETHYL ESTER
• N-BOC-4-METHYL-4-HYDROXY PIPERIDINE