ChemicalBook CAS DataBase List TERT-BUTYL 6-FORMYL-3-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLATE

TERT-BUTYL 6-FORMYL-3-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLATE synthesis

6synthesis methods

Product Name:TERT-BUTYL 6-FORMYL-3-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLATE
CAS Number:912468-67-8
Molecular formula:C11H17NO3
Molecular Weight:211.26

419572-18-2 Synthesis

exo-3-Boc-3-azabicyclo[3.1.0]hexane-6-methanol

419572-18-2
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TERT-BUTYL 6-FORMYL-3-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLATE

912468-67-8
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Yield:912468-67-8 80%

Reaction Conditions:

with Dess-Martin periodane in dichloromethane at 0; for 1 h;

Steps:

73.3 Step 3

To a solution of (1R,5S,6s)-tert-butyl 6-(hydroxymethyl)-3- azabicyclo[3.1.0]hexane-3-carboxylate (1.20 g, 5.63 mmol, 1.00 eq) in dichloromethane (30.0 mL) was added dess-martin periodinane (2.63 g, 6.19 mmol, 1.92 mL, 1.10 eq) at 0 °C. The mixture was stirred at 0 °C for 1 h. The mixture was diluted with water (5.00 mL) and saturated sodium carbonate (5.00 mL), extracted with dichloromethane (2 × 20.0 mL). The combined organic layers were washed with water (20.0 mL), dried over anhydrous sodium sulfate, filtered. The filtrate was concentrated to afford a residue. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate = 1/0~4/1) to afford tert-butyl 6-formyl-3-azabicyclo[3.1.0]hexane- 3- carboxylate (0.950 g, 4.50 mmol, 80% yield) as a colorless oil. ¹H NMR (400 MHz, Chloroform- d) d = 9.3 (d, J = 6.24 Hz, 1 H), 3.8 - 4.0 (m, 2 H), 3.6 - 3.7 (m, 2 H), 2.1 - 2.2 (m, 2 H), 1.7 - 1.8 (m, 1 H), 1.4 (s, 9 H).

References:

WO2021/30711,2021,A1 Location in patent:Paragraph 1159; 1161

850808-43-4 Synthesis