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[ CAS No. 870089-49-9 ]

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Chemical Structure| 870089-49-9
Chemical Structure| 870089-49-9
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CAS No. :870089-49-9 MDL No. :MFCD18073441
Formula : C10H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :199.25 g/mol Pubchem ID :59841137
Synonyms :

Safety of [ 870089-49-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 870089-49-9 ]

  • Upstream synthesis route of [ 870089-49-9 ]
  • Downstream synthetic route of [ 870089-49-9 ]

[ 870089-49-9 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
93%
Stage #1: at 0 - 20℃; for 3.66667 h;
Stage #2: at 0℃;
B.
Preparation of tert-butyl 3-acetylazetidine-1-carboxylate (C56).
A solution of C55 (27.1 g, 0.111 mol) in THF (200 mL) was added drop-wise to a 1.4M solution of methylmagnesium bromide in a mixture of THF and toluene (25:75) (99.0 mL, 0.139 mol) over 40 mins, while the reaction temp was kept at about 0° C.
After completion of the addition, the mixture was stirred at 10-15° C. for 2 hours, followed by 1 h at room temp.
The reaction mixture was cooled to 0° C. and quenched with a 10percent aqueous citric acid solution (150 mL).
The organic layer was separated, and the aqueous layer was extracted with EtOAc (2*300 mL).
The combined organic layers were washed with saturated aqueous sodium chloride solution (2*250 mL), and dried over sodium sulfate.
Filtration and removal of solvent gave a residue, which was purified by silica gel chromatography (Eluant: chloroform) to afford C56. Yield: 20.6 g, 0.10 mol, 93percent. 1H NMR (400 MHz, CDCl3): δ 4.04-4.02 (m, 4H), 3.43-3.35 (m, 1H), 2.16 (s, 3H), 1.42 (s, 9H).
93.4%
Stage #1: at 0 - 20℃; for 3.66667 h;
Stage #2: With water; citric acid In tetrahydrofuran; toluene at 0℃;
Preparation 85 tert-Butyl 3-acetylazetidine-1 -carboxylate; A solution of tert-butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate (Preparation 84, 27.1 g, 0.111 mol) in tetrahydrofuran (20OmL) was added dropwise to a 1.4 M solution of methylmagnesium bromide in a 25:75 mixture of tetrahydrofuran and toluene (99.0 mL, 0.139 mol, 1.25 eq) over 40 minutes. The reaction temperature was kept at ~0°C. After the addition, the mixture was stirred at 10-150C for 2 hours and then at room temperature for 1 hour. The mixture was cooled to 00C and 10percent aqueous citric acid (15OmL) was added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (60OmL). The organic layers were combined, washed with brine (50OmL) and dried using anhydrous sodium sulfate to give a residue which was purified by chromatography on silica gel, eluting with chloroform, to afford the title compound (20.6 g, 93.4percent).1H NMR (400 MHz, CDCI3): δ = 4.04-4.02 (m, 4H), 3.43-3.35 (m, 1 H), 2.16 (s, 3H), 1.42 (s, 9H) ppm.
77% at 0 - 20℃; for 17 h; Methylmagnesium bromide (3M solution in THF, 10.4 mL, 31.3 mmol) was added dropwise to a cooled (0° C.) solution of tert-butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate (87a, 5.1 g, 20.88 mmol) in anhydrous THF (100 mL). Stirring was continued at 0° C. for one hour, then at room temperature for 16 hours. The mixture was cooled to 0° C. and quenched with sat. aq. NaHCO3 (35 mL), then extracted with ethyl acetate (3×40 mL). The combined organic extracts were washed with brine (3×40 mL), dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography (eluting with petroleum ether/ethyl acetate from 10:1 to 3:1) to give tert-butyl 3-acetylazetidine-1-carboxylate (87b, (3.20 g, 77percent yield) as light yellow oil. 1H NMR (400 MHz, CDCl3) δ 4.05 (d, J=7.6 Hz, 4H), 3.41 (quint, J=7.6 Hz, 1H), 2.18 (s, 3H), 1.43 (s, 9H).
Reference: [1] Patent: US2010/190771, 2010, A1, . Location in patent: Page/Page column 31-32
[2] Patent: WO2010/131145, 2010, A1, . Location in patent: Page/Page column 87
[3] Patent: US2015/361067, 2015, A1, . Location in patent: Paragraph 0621
[4] Patent: WO2018/137573, 2018, A1, . Location in patent: Page/Page column 65; 66
[5] Patent: WO2014/173289, 2014, A1, . Location in patent: Paragraph 0296; 0300; 0301
[6] Patent: TWI602818, 2017, B, . Location in patent: Paragraph 0300; 0301
  • 2
  • [ 1309208-79-4 ]
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YieldReaction ConditionsOperation in experiment
100% With acetic acid In 1,4-dioxane; water at 100 - 110℃; for 0.5 h; Microwave irradiation Step 3: 3-Acetyl-azetidine-l-carboxylic acid tert- butyl esterA solution of 3-(2,2-dimethyl-4,6-dioxo-[l,3]dioxane-5-carbonyl)-azetidine-l- carboxylic acid terf-butyl ester (1.0 g, 3.05 mmol) in a mixture of actic acid (0.5 mL), water 0.25 mL and dioxane (3 mL) was stirred under microwaves at 100°C for 30 minutes. After concentration to dryness, the residue was coeveoparted with dichloromethane (2 x 100 mL). The title product was obtained as a colorless gum (600 mg, 100percent).LCMS (ESI-APCI) m/z 308.2 (M + H)+
70% With acetic acid In 1,4-dioxane; water at 150℃; for 0.5 h; Microwave irradiation To a stirring solution of compound 1 (2.8 g, 8.6 mmol) in dry dioxane (20 mL) was added AcOH (1.5 mL) and H20 (0.75 mL), then stirred at 150 °C for 30 mm with microwave heating.Quenched with water, extracted with EtOAc, concentrated under reduced pressure to obtain cmde product, which was purified by combiflash (methanol:DCM = 1:20) to give compound 2 (1.2 g, 70percent). LC-MS: m/z = 100.0 [M+H-Boc]
Reference: [1] Patent: WO2011/61214, 2011, A1, . Location in patent: Page/Page column 147-148
[2] Patent: WO2016/44770, 2016, A1, . Location in patent: Page/Page column 738
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  • [ 820971-67-3 ]
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Reference: [1] Patent: US2008/58348, 2008, A1, . Location in patent: Page/Page column 13
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  • [ 820971-67-3 ]
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  • [ 870089-49-9 ]
Reference: [1] Patent: WO2009/45382, 2009, A1, . Location in patent: Page/Page column 53
  • 5
  • [ 142253-55-2 ]
  • [ 870089-49-9 ]
Reference: [1] Patent: WO2014/173289, 2014, A1,
[2] Patent: TWI602818, 2017, B,
[3] Patent: WO2018/137573, 2018, A1,
[4] Patent: US2015/361067, 2015, A1,
[5] Patent: US2008/58348, 2008, A1,
[6] Patent: WO2011/61214, 2011, A1,
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  • [ 24424-99-5 ]
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Reference: [1] Patent: WO2011/61214, 2011, A1,
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