ChemicalBook CAS DataBase List tert-butyl 9-oxo-3-azabicyclo[3.3.1]nonane-3-carboxylate

tert-butyl 9-oxo-3-azabicyclo[3.3.1]nonane-3-carboxylate synthesis

2synthesis methods

Product Name:tert-butyl 9-oxo-3-azabicyclo[3.3.1]nonane-3-carboxylate
CAS Number:512822-34-3
Molecular formula:C13H21NO3
Molecular Weight:239.31

24424-99-5 Synthesis

24424-99-5
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86949-84-0
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tert-butyl 9-oxo-3-azabicyclo[3.3.1]nonane-3-carboxylate

512822-34-3
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$208.33/0.25g

Yield:512822-34-3 0.3 g

Reaction Conditions:

with diisopropylamine in dichloromethane at 20; for 1 h;

Steps:

Step 2.

To a crude solution of 3-azabicyclo[3.3.1]nonan-9-one (0.35 g, 1.0 eq., 2.51 mmol) in dry DCM (5.0 mL) were sequentially added di-tert-butyl dicarbonate (0.656 g, 1.2 eq., 3.01 mmol) and diisopropyl amine (1.31 mL, 3.0 eq., 7.53 mmol). The resulting mixture was stirred at room temperature for 1 h. The reaction was then quenched with water and the organics extracted with DCM (220 mL). The organic phase was dried over Na₂SO₄and concentrated in vacuo to furnish a crude product, which was purified by flash chromatography eluting with cyclohexane/EtOAc (8:2) to give the pure tert-butyl 9-oxo-3-azabicyclo[3.3.1]nonane-3-carboxylate as a pale yellow solid (0.3 g, 50% estimated). UPLC-MS: t_R=2.23 min (generic method); MS (ESI) m/z calcd for C₉H₁₄NO₃(M-^tBu+2H)⁺: 184.1, found: 184.1. ¹H NMR (400 MHz, DMSO-d₆) 4.43-4.18 (m, 2H), 3.35-3.10 (m, 2H), 2.27 (br s, 2H), 2.17-2.03 (m, 2H), 1.99-1.82 (m, 3H), 1.49-1.45 (m, 1H), 1.44 (s, 9H).

References:

US2019/135778,2019,A1 Location in patent:Paragraph 0107

81879-64-3 Synthesis

81879-64-3
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512822-34-3
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$208.33/0.25g

References