tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate Chemical Properties

Melting point:

127-129℃

Boiling point:

316.6±42.0 °C(Predicted)

Density 

1.17

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

14.84±0.20(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C11H19NO3/c1-10(2,3)15-9(14)12-6-11(7-12)4-8(13)5-11/h8,13H,4-7H2,1-3H3

InChIKey

UMXXHZDEAZUQKZ-UHFFFAOYSA-N

SMILES

C1C2(CC(O)C2)CN1C(OC(C)(C)C)=O

Safety Information

HS Code 

2934999090

tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate Usage And Synthesis

Uses

tert-?Butyl 6-?Hydroxy-?2-?azaspiro[3.3]?heptane-?2-?carboxylate is a reactant used in the synthesis of pharmaceuticals such as CNS penetrant CXCR2 antagonists for the potential treatment of CNS demyelinating.

Synthesis

Step 8: Synthesis of tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate At 0 °C and under nitrogen protection, tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate (507 mg, 2.4 mmol) was dissolved in methanol (5.0 mL) and sodium borohydride (182 mg, 4.8 mmol) was added slowly. The reaction mixture was stirred at 0 °C for 30 min. After completion of the reaction, the solvent was concentrated in vacuum by rotary evaporator to give the crude product. Saturated sodium bicarbonate solution (30 mL) was added to the crude product and the aqueous phase was extracted with dichloromethane (4 x 30 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated in vacuum to afford tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate (5 mg, 100% yield) as a white solid.1H NMR (300 MHz, CDCl3): δ 4.18 (m, 1H), 3.88 (d, 4H), 2.53 (m, 2H), 2.08 (m. 2H), 1.42 (s, 9H).

References

[1] Patent: WO2013/13308, 2013, A1. Location in patent: Paragraph 00178-00180
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5663 - 5672
[3] Patent: CN106565706, 2017, A. Location in patent: Paragraph 0179; 0180; 0181
[4] Patent: EP3281942, 2018, A1. Location in patent: Paragraph 0105; 0106
[5] Patent: WO2018/133858, 2018, A1. Location in patent: Paragraph 00221

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