Category: 335599-07-0

Synthetic Route of 335599-07-0,Some common heterocyclic compound, 335599-07-0, name is Ethyl 3-oxa-bicyclo[3.1.0]hexane-6-carboxylate, molecular formula is C8H12O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(3-Oxa-bicyclo[3.1.0]hex-6-yl)-methanol (56)-A 1M solution of LiAlH4 in THF (16.77 mL, 16.77 mmol) was cooled in an ice-water/acetone bath and a solution of 56 (2.62 g, 16.77 mmol) in THF (25 mL) was added slowly with stirring. The reaction was warmed to RT over 30 min and stirred for 1 h. The reaction was quenched by slow portionwise addition of 4.8 g of Na2SO4.10H2O, Stirring was continued for additional 1 h after the vigorous reaction subsided. MgSO4 was added and solids were removed by filtration, rinsed with fresh THF and solvents evaporated. The residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (0 to 50% EtOAc) to afford 0.98 g (51.3%) of 56 as a colorless liquid.

The synthetic route of 335599-07-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rotstein, David Mark; Melville, Chris Richard; US2008/249087; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 335599-07-0, name is Ethyl 3-oxa-bicyclo[3.1.0]hexane-6-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: Ethyl 3-oxa-bicyclo[3.1.0]hexane-6-carboxylate

Production Example 11-2(3-Oxa-bicyclo[3.1.0]hex-6-yl)methanol diastereomer 1 3-Oxa-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester diastereomer 1 (10 g, 64.1 mmol) was dissolved in TIM (100 mL), and to the mixture, was added dropwise a 0.99M toluene (180 mL, 178 mmol) solution of DIBAL while cooling on ice, and stirred at room temperature for one hour. To the reaction mixture, were added a small amount of water and ethyl acetate, and the mixture was filtered with Celite, washed with ethyl acetate, and then the filtrate was distilled off under reduced pressure, and the residue was purified by column chromatography (heptane:ethyl acetate to 75% ethyl acetate) to obtain the title compound (2.6 g, 228 mmol) as a colorless oil.1H-NMR (CDCl3) delta: 1.10 (dt, J=3.6 Hz, 6.8 Hz, 1H), 1.53-1.56 (m, 2H), 3.53 (d, J=6.8 Hz, 2H), 3.70 (d, J=8.0 Hz, 2H), 3.88 (d, J=8.4 Hz, 2H)Production Example 11-3(3-Oxa-bicyclo[3.1.0]hex-6-yl)methanol diastereomer 2 From 3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester diastereomer 2 (5 g, 32.1 mmol), the title compound (2.1 g, 18.4 mmol) was obtained as a colorless oil according to the same procedure as in (3-oxa-bicyclo[3.1.0]hex-6-yl)methanol diastereomer 1.1H-NMR (CDCl3) delta: 1.23 (t, J=3.6 Hz, 1H), 1.80 (d, J=3.6 Hz, 2H), 3.79 (d, J=7.6 Hz, 2H), 3.91 (m, 4H)

The synthetic route of Ethyl 3-oxa-bicyclo[3.1.0]hexane-6-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2011/86882; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics