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Chemical Structure| 1401031-37-5
Chemical Structure| 1401031-37-5
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Product Details of [ 1401031-37-5 ]

CAS No. :1401031-37-5 MDL No. :N/A
Formula : C16H20N2O Boiling Point : -
Linear Structure Formula :- InChI Key :AJVYDBCIZBRGAK-UHFFFAOYSA-N
M.W : 256.34 Pubchem ID :68313710
Synonyms :

Safety of [ 1401031-37-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1401031-37-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1401031-37-5 ]

[ 1401031-37-5 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 1401031-36-4 ]
  • [ 1401031-37-5 ]
YieldReaction ConditionsOperation in experiment
90% With potassium hydroxide In ethylene glycol at 120℃; for 4h; Preparation of 2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl)acetonitrile (5) To a solution of methyl 2-cyano-2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9- yl)acetate (4 g, 12.7 mmol) and KOH (1.4 g, 25.4 mmol) was added in ethylene glycol (50 mL). The solution was stirred at 120 °C for 4 hours. The reaction mixture was slowly quenched with water (100 mL) and the mixture was extracted with EtOAc (2 x 100 mL). The combined organic layers were dried over Na2S04, filtered and concentrated. The crude product was purified via flash chromatography (Si02; 4: 1 hexanes:EtOAc) to give 2-(9-(pyridin-2-yl)-6- oxaspiro[4.5]decan-9-yl)acetonitrile as a white solid. (3 g, 90 % yield, 1H NMR confirmed).
90% With potassium hydroxide In ethylene glycol at 120℃; for 4h; Preparation of 2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl)acetonitrile (5) To a solution of methyl 2-cyano-2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl)acetate (4 g, 12.7 mmol) and KOH (1.4 g, 25.4 mmol) was added in ethylene glycol (50 mL). The solution was stirred at 120 °C for 4 hours. The reaction mixture was slowly quenched with water (100 mL) and the mixture was extracted with EtOAc (2 x 100 mL). The combined organic layers were dried over Na2S04, filtered and concentrated. The crude product was purified via flash chromatography (S1O2; 4: 1 hexanes:EtOAc) to give 2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl)acetonitrile as a white solid. (3 g, 90 % yield, l NMR confirmed).
82% With potassium hydroxide In ethylene glycol at 120℃; for 3h; 15 2-[9-(Pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile Ethylene glycol (300 ml) was added to methyl 2-cyano-2-[9-(pyridin-2-yl)-6- oxaspiro[4.5] decan-9-yl]acetate( 15.43 g, 49 mmol) followed by potassium hydroxide (5.5 g, 98 mmol), the resulting mix was heated to l2OoC, after 3 h, the reaction mix was cooled and water (300 ml) was added, the product was extracted by Et20(3 x 400 ml), washed with water(200 ml), dried (Na2SO4) and concentrated, the residual was purified by flash chromatography (340 g silica gel column, eluted by EtOAc in hexane: 3% 2CV; 3-25%, 12 CV; 25-40% 6CV to give 2-[9-(Pyridin-2-yl)-6-oxaspiro[4.5]decan-9- yl]acetonitrile (10.37 g, 82% yield, m/z 257.0 [M + H]+ observed)
66% With potassium hydroxide In ethylene glycol at 120℃; for 3h;
60% With potassium hydroxide In 1,2-dimethoxyethane at 120℃; for 5h; 1.5 Step 5: 2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decane-9-yl)acetonitrile (1f) Ethylene glycol (20mL)Addition to methyl 2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decane-9-yl)acetate(1e) (1.57g, 4.99mmol),Then potassium hydroxide (0.56 g, 9.99 mmol) was added.After the addition, the reaction solution was heated to 120 ° C for 5 hours.The reaction mixture was cooled to room temperature and water (60 mL) was added.The product was extracted with EtOAc (EtOAc (EtOAc)EtOAc.After mixing (EA:PET=1: 80-1:50)Purified by column to obtain oily liquid2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decane-9-yl)acetonitrile (1f) (0.8 g, yield: 60%).

  • 2
  • [ 855398-57-1 ]
  • [ 1401031-37-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ammonium acetate; acetic acid / benzene / Reflux; Dean-Stark 2: copper(l) iodide / tetrahydrofuran; diethyl ether / 0.5 h / 20 °C / Cooling with ice 3: potassium hydroxide / ethylene glycol / 3 h / 120 °C
Multi-step reaction with 3 steps 1.1: ammonium acetate; acetic acid / toluene / 4 h / Reflux; Dean-Stark 2.1: isopropylmagnesium chloride / tetrahydrofuran / 4.5 h / 0 - 20 °C 2.2: 0.5 h / 20 °C 2.3: 16 h / 20 °C 3.1: potassium hydroxide / ethylene glycol / 4 h / 120 °C
Multi-step reaction with 3 steps 1.1: acetic acid; ammonium acetate / benzene / 3 h / Dean-Stark; Reflux 2.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / 20 °C 2.3: 18.5 h / 20 °C 3.1: potassium hydroxide / ethylene glycol / 3 h / 120 °C
Multi-step reaction with 3 steps 1.1: acetic acid; ammonium acetate / toluene / 4 h / Dean-Stark; Reflux 2.1: isopropylmagnesium chloride / tetrahydrofuran / 4.5 h / 0 - 20 °C 2.2: 0.5 h / 20 °C 2.3: 16 h / 20 °C 3.1: potassium hydroxide / ethylene glycol / 4 h / 120 °C
Multi-step reaction with 3 steps 1.1: ammonium acetate; acetic acid / toluene / 6 h / Reflux 2.1: isopropylmagnesium chloride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / 20 °C / Inert atmosphere 2.3: 8 h / 55 °C / Inert atmosphere 3.1: potassium hydroxide / 1,2-dimethoxyethane / 5 h / 120 °C
Multi-step reaction with 3 steps 1: ammonium acetate; acetic acid / toluene / Dean-Stark; Reflux 2: copper(l) iodide / diethyl ether / 3 h / 0 °C 3: potassium hydroxide / ethylene glycol / 3 h / 120 °C

  • 3
  • [ 1467617-14-6 ]
  • [ 1401031-37-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide / tetrahydrofuran; diethyl ether / 0.5 h / 20 °C / Cooling with ice 2: potassium hydroxide / ethylene glycol / 3 h / 120 °C
Multi-step reaction with 2 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 4.5 h / 0 - 20 °C 1.2: 0.5 h / 20 °C 1.3: 16 h / 20 °C 2.1: potassium hydroxide / ethylene glycol / 4 h / 120 °C
Multi-step reaction with 2 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C 1.3: 18.5 h / 20 °C 2.1: potassium hydroxide / ethylene glycol / 3 h / 120 °C
Multi-step reaction with 2 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 4.5 h / 0 - 20 °C 1.2: 0.5 h / 20 °C 1.3: 16 h / 20 °C 2.1: potassium hydroxide / ethylene glycol / 4 h / 120 °C
Multi-step reaction with 2 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 1.3: 8 h / 55 °C / Inert atmosphere 2.1: potassium hydroxide / 1,2-dimethoxyethane / 5 h / 120 °C

  • 4
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 5
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / diethyl ether / 0 °C 2: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 6
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 7
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 8
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 9
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 10
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 11
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 12
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 13
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 14
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 15
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 16
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 17
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 18
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 19
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 20
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 21
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 22
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 23
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 24
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 25
  • [ 1401031-37-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C
  • 26
  • [ 1401031-37-5 ]
  • [ 1401031-38-6 ]
  • [ 1467617-38-4 ]
YieldReaction ConditionsOperation in experiment
1: 40% 2: 42% With AD-H column In methanol; diethylamine Resolution of racemate;
4 g With Column: Chiralpak AD-H Resolution of racemate; 4 Step 4. Synthesis of Compound 6 The racemic 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile 5 was separated by chiral HPLC column under the following preparative-SFC conditions: Instrument: SFC-80 (Thar, Waters); Column: Chiralpak AD-H (D aicel); column temperature: 40 °C; Mobile phase: (0435) Methanol/CO2=40/60; Flow: 70 g/min; Back pressure: 120 Bar; Cycle time of stack injection: (0436) 6.0min; Load per injection: 225 mg; Under these conditions, 2-[9-(pyridin-2-yl)-6- oxaspiro[4.5]decan-9-yl]acetonitrile 6 (4.0 g) was separated to provide the desired isomer.
1: 10.79 g 2: 11.17 g With Chiralpak AD In methanol at 38℃; for 0.116667h; Resolution of racemate; enantioselective reaction; 1.6 (S)-2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decane-9-yl)acetonitrile (1g-2) Resolution of the compound 2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decane-9-yl)acetonitrileTake 2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decane-9-yl)acetonitrile (30 g)For resolution, separation gives two optical isomer compounds(R)-2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decane-9-yl)acetonitrile (1 g-1) (4.04 min, 10.79 g, white solid, ee% = 99.7%),Compound (S)-2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decane-9-yl)acetonitrile(1 g-2) (retention time: 2.00 min, 11.17 g, white solid, ee% = 99.6%).Split conditions:Instrument: Thar 350preparative SFC (SFC-9);Column: Chiralpak AD, 300 × 50 mm I.D., 10 μm; mobile phase: A: CO2, B:Methanol; gradient: B 45%; flow rate: 200 mL/min; back pressure: 100 bar; columnTemperature: 38 ° C; wavelength: 220 nm; period: 7 min;Compound (1F) was dissolved in methanol to prepare 60 mg/ml; injection: 15 ml/needle.
  • 27
  • [ 1401031-37-5 ]
  • [ 1401026-78-5 ]
YieldReaction ConditionsOperation in experiment
77% With lithium aluminium tetrahydride In diethyl ether at 0℃; for 2h; 1.6 Step 6: Preparing 2-(9-(pyridin-2-yl)-6-oxaspiro [4.5]decan-9-yl)ethylamine (1c) Lithium aluminum tetrahydride (120 mg, 3 mmol) was added into a solution of 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile (1b, 256 mg, 1.0 mmol) in anhydrous diethyl ether (15 ml) at 0°C. After 2 hours, water(0.1 ml) and 15% aqueous sodium hydroxide solution (0.1 ml) were added into the reaction solution respectively, andthen quenched with water (0.1 ml). The reaction mixture was extracted with diethyl ether (3 3 20 ml), dried with anhydrousmagnesium sulfate, filtered then concentrated to obtain 2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl) ethylamine (1c,200 mg), with a yield of: 77%, as a yellow oily substance, which was used without further purification.1H NMR (400 MHz, CDCl3) ppm 8.58 (ddd, J =4.8, 1.9, 0.9, 1H), 7.63 (m, 1H),7.30 (m, 1H), 7.12 (ddd, J =7.4, 4.8, 1.0,1H), 3.76 (m,2H), 2.55 (td, J ∼ 11.6, 5.1, 1H), 2.46 (ddd, J = 13.7,5.1, 2.7, 1H), 2.37 (dd, J = 13.7, 2.1, 1H), 2.14 (td, J=11.6,5.0, 1H), 1.92 (m, 2H), 1.70 (m, 4H), 1.46 (m,4H), 1.13 (m, 1H), 0.71 (dt, J =13.4, 8.8, 1H). LC-MS: m/z (ES+)was calculated to be C16H24N2O 261[M+1]+
With lithium aluminium tetrahydride In diethyl ether at 0℃;
  • 28
  • [ 1401031-37-5 ]
  • [ 1467616-57-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / diethyl ether / 0 °C 2: sodium sulfate / dichloromethane / 4 h / 20 °C 3: sodium tetrahydroborate / methanol / 1 h / 0 °C
  • 29
  • [ 1401031-37-5 ]
  • [ 1467617-03-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C 4: sodium tetrahydroborate / methanol / 1 h / 0 °C
  • 30
  • [ 1401031-37-5 ]
  • [ 1467617-05-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C 4: sodium tetrahydroborate / methanol / 1 h / 0 °C
  • 31
  • [ 1401031-37-5 ]
  • [ 1467616-59-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C 4: sodium tetrahydroborate / methanol / 1 h / 0 °C
  • 32
  • [ 1401031-37-5 ]
  • [ 1467616-61-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: sodium sulfate / dichloromethane / 4 h / 20 °C 4: sodium tetrahydroborate / methanol / 1 h / 0 °C
  • 33
  • [ 1401031-37-5 ]
  • [ 1401026-79-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: AD-H column / methanol; diethylamine / Resolution of racemate 2: lithium aluminium tetrahydride / diethyl ether / 0 °C
Multi-step reaction with 2 steps 1: Resolution of racemate 2: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C
Multi-step reaction with 2 steps 1.1: Column: Chiralpak AD-H (Daicel) / methanol; carbon dioxide / 40 °C / Supercritical conditions; liquid CO2 2.1: ammonia / methanol / 0.25 h / Autoclave 2.2: Raney-Nickel / 72 h / 25 - 50 °C / 1551.49 - 4654.46 Torr / Inert atmosphere
Multi-step reaction with 2 steps 1: Column: Chiralpak AD-H / Resolution of racemate 2: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: Chiralpak AD / methanol / 0.12 h / 38 °C / Resolution of racemate 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

  • 34
  • [ 1401031-37-5 ]
  • [ 1401031-38-6 ]
YieldReaction ConditionsOperation in experiment
45% Resolution of racemate; 1 Preparation of (R)-2-(9-(pyridin-2-yl)-6-oxaspiro[4. 5]decan-9-yl)acetonitrile (6) To a soution of 2-(9-(pyridin-2-y)-6-oxaspiro[4.5]decan-9-y)acetonitrie (6.5 g, was purified by Chira separation to give (R)-2-(9-(pyridin-2-y)-6-oxaspiro[4.5] decan-9- y)acetonitrie as a white soid. (3 g, 45 % yied, ‘H NMR confirmed)
2 g With Column: Chiralpak AD-H (Daicel) In methanol; carbon dioxide at 40℃; Supercritical conditions; liquid CO2; 15 2-(9R)-9-(Pyridin-2-yl)-6-oxaspiro[4.5] decan-9-yl]acetonitrile The racemic 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5] decan-9-yl] acetonitrile was separated by chiral HPLC column under the following preparative-SFC conditions:Instrument: SFC-80 (Thar, Waters); Column: Chiralpak AD-H (Daicel); column temperature: 40 °C; Mobile phase: Methanol /C02=40/60; Flow: 70 g/min; Back pressure: 120 Bar; Cycle time of stack injection: 6.0mm; Load per injection: 225 mg; Under these conditions, 2- [9-(pyridin-2-yl)-6-oxaspiro[4.5 ]decan-9-yl] acetonitrile (4.0 g) was separated to provide the desired isomer, 2-[(9R)-9-(Pyridin-2-yl)-6- oxaspiro[4.5]decan-9-yl]acetonitrile (2.0 g, >99.5% enantiomeric excess) as a slowmoving fraction. The absolute (R) configuration of the desired isomer was later determined by an X-ray crystal structure analysis of Compound 140
  • 35
  • [ 1401031-37-5 ]
  • [ 2101640-96-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Resolution of racemate 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 3.1: sodium sulfate / dichloromethane / 14 h / 20 °C 3.2: 0.5 h / 20 °C 3.3: 4 h / 20 °C
Multi-step reaction with 3 steps 1.1: Column: Chiralpak AD-H / Resolution of racemate 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 3.1: sodium sulfate / dichloromethane / 14 h / 20 °C 3.2: 0.5 h / 20 °C 3.3: 4 h / 20 °C
  • 36
  • [ 120-92-3 ]
  • [ 1401031-37-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: trifluoroacetic acid / dichloromethane / 13 h / 0 - 20 °C 2.1: silica gel; pyridinium chlorochromate / tetrahydrofuran / 12 h / 20 °C 3.1: ammonium acetate; acetic acid / toluene / 4 h / Reflux; Dean-Stark 4.1: isopropylmagnesium chloride / tetrahydrofuran / 4.5 h / 0 - 20 °C 4.2: 0.5 h / 20 °C 4.3: 16 h / 20 °C 5.1: potassium hydroxide / ethylene glycol / 4 h / 120 °C
Multi-step reaction with 5 steps 1.1: trifluoroacetic acid / dichloromethane / 13 h / 0 - 20 °C 2.1: silica gel; pyridinium chlorochromate / tetrahydrofuran / 12 h / 20 °C 3.1: acetic acid; ammonium acetate / toluene / 4 h / Dean-Stark; Reflux 4.1: isopropylmagnesium chloride / tetrahydrofuran / 4.5 h / 0 - 20 °C 4.2: 0.5 h / 20 °C 4.3: 16 h / 20 °C 5.1: potassium hydroxide / ethylene glycol / 4 h / 120 °C
Multi-step reaction with 5 steps 1.1: sulfuric acid / 12 h / 0 - 20 °C 2.1: Dess-Martin periodane / dichloromethane / 12 h / 0 - 20 °C 3.1: ammonium acetate; acetic acid / toluene / 6 h / Reflux 4.1: isopropylmagnesium chloride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 4.2: 0.5 h / 20 °C / Inert atmosphere 4.3: 8 h / 55 °C / Inert atmosphere 5.1: potassium hydroxide / 1,2-dimethoxyethane / 5 h / 120 °C
Multi-step reaction with 5 steps 1: sulfuric acid / 0 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 20 °C 3: ammonium acetate; acetic acid / toluene / Dean-Stark; Reflux 4: copper(l) iodide / diethyl ether / 3 h / 0 °C 5: potassium hydroxide / ethylene glycol / 3 h / 120 °C

  • 37
  • [ 855398-58-2 ]
  • [ 1401031-37-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: silica gel; pyridinium chlorochromate / tetrahydrofuran / 12 h / 20 °C 2.1: ammonium acetate; acetic acid / toluene / 4 h / Reflux; Dean-Stark 3.1: isopropylmagnesium chloride / tetrahydrofuran / 4.5 h / 0 - 20 °C 3.2: 0.5 h / 20 °C 3.3: 16 h / 20 °C 4.1: potassium hydroxide / ethylene glycol / 4 h / 120 °C
Multi-step reaction with 4 steps 1.1: silica gel; pyridinium chlorochromate / tetrahydrofuran / 12 h / 20 °C 2.1: acetic acid; ammonium acetate / toluene / 4 h / Dean-Stark; Reflux 3.1: isopropylmagnesium chloride / tetrahydrofuran / 4.5 h / 0 - 20 °C 3.2: 0.5 h / 20 °C 3.3: 16 h / 20 °C 4.1: potassium hydroxide / ethylene glycol / 4 h / 120 °C
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 12 h / 0 - 20 °C 2.1: ammonium acetate; acetic acid / toluene / 6 h / Reflux 3.1: isopropylmagnesium chloride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 3.2: 0.5 h / 20 °C / Inert atmosphere 3.3: 8 h / 55 °C / Inert atmosphere 4.1: potassium hydroxide / 1,2-dimethoxyethane / 5 h / 120 °C
Multi-step reaction with 4 steps 1: pyridinium chlorochromate / dichloromethane / 20 °C 2: ammonium acetate; acetic acid / toluene / Dean-Stark; Reflux 3: copper(l) iodide / diethyl ether / 3 h / 0 °C 4: potassium hydroxide / ethylene glycol / 3 h / 120 °C

  • 38
  • [ 1401031-37-5 ]
  • [ 1401031-28-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Column: Chiralpak AD-H (Daicel) / methanol; carbon dioxide / 40 °C / Supercritical conditions; liquid CO2 2: diisobutylaluminium hydride / toluene / 1.5 h / -78 °C
Multi-step reaction with 2 steps 1: Column: Chiralpak AD-H / Resolution of racemate 2: diisobutylaluminium hydride / toluene / 2 h / -78 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: Chiralpak AD / methanol / 0.12 h / 38 °C / Resolution of racemate 2: diisobutylaluminium hydride; propan-2-one / toluene / 3 h / -70 °C
Multi-step reaction with 5 steps 1.1: potassium hydroxide / ethylene glycol / 24 h / 110 °C / Large scale 2.1: ethanol / 2 h / 50 °C / Reflux 3.1: potassium hydroxide / lithium hydroxide monohydrate 4.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; 4-dimethylaminopyridine / dichloromethane 4.2: 20 °C / Inert atmosphere 5.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / -45 - -35 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: sulfuric acid / lithium hydroxide monohydrate / 1 h / 10 - 50 °C 2: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / 0 - 45 °C / Inert atmosphere 3: 1,1'-binaphthyl-2,2'-dihydrogen phosphate / tetrahydrofuran / 1 h / 20 °C 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C
Multi-step reaction with 5 steps 1: sulfuric acid / lithium hydroxide monohydrate / 1 h / 10 - 50 °C 2: dichlorosulfoxide / 3 h / 5 - 55 °C / Inert atmosphere 3: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1.5 h / 0 - 45 °C / Inert atmosphere 4: 1,1'-binaphthyl-2,2'-dihydrogen phosphate / tetrahydrofuran / 1 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C

  • 39
  • [ 1401031-37-5 ]
  • [ 2095345-20-1 ]
YieldReaction ConditionsOperation in experiment
53.4% Stage #1: 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile With diisobutylaluminium hydride In toluene at -78℃; for 1.5h; Stage #2: With hydrogenchloride In toluene for 0.5h; 18.1 Step 1 2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl)acetaldehyde 18b 2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl)acetonitrile 18a (500 mg, 1.95 mmol, prepared by a method diclosed in the patent application "WO2012129495") wasdissolved in 20 mL of toluene, 4.2 mL of 1 M diisobutylaluminum hydride solution was slowly added dropwise at -78°C,and the reaction was stirred for 1.5 hours. Then, 18 mL of 2 M hydrochloric acid was added, and the mixture was stirredfor 30 minutes. 5 M sodium hydroxide solution was added dropwise until the pH of the reaction soultion was 9 to 10.The mixture was warmed up to room temperature and extracted with ethyl acetate (30 mL33). The organic phases werecombined, washed with saturated sodium chloride solution (30 mL33), dried over anhydrous sodium sulfate and filtered.The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatographywith elution system A to obtain the title compound 18b (270 mg, yield 53.4%) as a yellow oil.MS m/z (ESI): 260.5 [M+1]
  • 40
  • [ 1401031-37-5 ]
  • [ 2314459-25-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Chiralpak AD / methanol / 0.12 h / 38 °C / Resolution of racemate 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 3.1: sodium sulfate / dichloromethane / 20 °C 3.2: 2 h
Multi-step reaction with 4 steps 1.1: Chiralpak AD / methanol / 0.12 h / 38 °C / Resolution of racemate 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 3.1: sodium sulfate / dichloromethane / 20 °C 3.2: 2 h 4.1: hydrogenchloride / methanol / 1 h / 20 °C
  • 41
  • [ 1401031-37-5 ]
  • [ 2314460-79-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Chiralpak AD / methanol / 0.12 h / 38 °C / Resolution of racemate 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 3.1: sodium sulfate / dichloromethane / 20 °C 3.2: 2 h 4.1: triethylamine / dichloromethane / 5 h / 20 °C
Multi-step reaction with 5 steps 1.1: Chiralpak AD / methanol / 0.12 h / 38 °C / Resolution of racemate 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 3.1: sodium sulfate / dichloromethane / 20 °C 3.2: 2 h 4.1: hydrogenchloride / methanol / 1 h / 20 °C 5.1: triethylamine / dichloromethane / 5 h / 20 °C
  • 42
  • [ 1401031-37-5 ]
  • [ 2314460-80-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: Chiralpak AD / methanol / 0.12 h / 38 °C / Resolution of racemate 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 3.1: sodium sulfate / dichloromethane / 20 °C 3.2: 2 h 4.1: triethylamine / dichloromethane / 5 h / 20 °C 5.1: triethylamine / dichloromethane / 2 h / 0 °C
Multi-step reaction with 6 steps 1.1: Chiralpak AD / methanol / 0.12 h / 38 °C / Resolution of racemate 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 3.1: sodium sulfate / dichloromethane / 20 °C 3.2: 2 h 4.1: hydrogenchloride / methanol / 1 h / 20 °C 5.1: triethylamine / dichloromethane / 5 h / 20 °C 6.1: triethylamine / dichloromethane / 2 h / 0 °C
  • 43
  • [ 1401031-37-5 ]
  • [ 2314459-05-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: Chiralpak AD / methanol / 0.12 h / 38 °C / Resolution of racemate 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 3.1: sodium sulfate / dichloromethane / 20 °C 3.2: 2 h 4.1: triethylamine / dichloromethane / 5 h / 20 °C 5.1: triethylamine / dichloromethane / 2 h / 0 °C 6.1: hydrogenchloride / ethyl acetate / 2 h / 0 - 20 °C
Multi-step reaction with 7 steps 1.1: Chiralpak AD / methanol / 0.12 h / 38 °C / Resolution of racemate 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 3.1: sodium sulfate / dichloromethane / 20 °C 3.2: 2 h 4.1: hydrogenchloride / methanol / 1 h / 20 °C 5.1: triethylamine / dichloromethane / 5 h / 20 °C 6.1: triethylamine / dichloromethane / 2 h / 0 °C 7.1: hydrogenchloride / ethyl acetate / 2 h / 0 - 20 °C
  • 44
  • [ 1401031-37-5 ]
  • [ 74-88-4 ]
  • [ 2300115-54-0 ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile; methyl iodide With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; 26.1 Step 1: Preparing 2- [9- (pyridin-2-yl) -6-oxaspiro [4.5] decan-9-yl] propionitrile (26a) 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile (1b, 0.256 g, 1 mmol) was dissolved in anhydrous N,N-dimethylformamide (10 mL), cooled to 0°C, sodium hydride (60mg, 1.5mmol) was added thereto, the reaction wascontinued at 0 °C for 30 minutes, then methyl iodide (284mg, 2mmol) was added, and the mixture was slowly warmedto room temperature and kept overnight. The reaction solution was quenched by adding ice water (10 mL) thereto, andextracted with ethyl acetate (15 mL33), the organic layer was washed with water (15 mL33), washed with saturatedsodium chloride (15 mL), dried and concentrated, the yellow solid compound 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl] propionitrile (26a, 0.2 g) was obtained by silica gel column (developing solvent was 5% to 40% ethyl acetate/nhexane),yield 74%
  • 45
  • [ 1401031-37-5 ]
  • [ 1956371-60-0 ]
YieldReaction ConditionsOperation in experiment
90% With potassium hydroxide In ethylene glycol at 110℃; for 24h; Large scale; 1.1; 2.1 Step One: Synthesis of Intermediate (D-1) The compound represented by the formula (E1) (13.5 kg, 1.0 eq), potassium hydroxide (2.6 kg, 2.0 eq) and ethylene glycol (135 L, 10 vol) were mixed, and the mixture was heated to 110° C. and stirred for 24 hours, and then the reaction was stopped. The resulting mixture was concentrated under reduced pressure to remove ethanol, then dichloromethane (26 L) was added to the residue and the mixture was stirred for dissolution. The mixture was washed twice with saturated sodium chloride solution (5 L), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the product (13 kg, yellow oil) with a yield of 90% and a HPLC purity of 95%.
60% With potassium hydroxide In lithium hydroxide monohydrate; ethylene glycol at 100℃; 19.1 Step 1: Preparing 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl] acetic acid (19a) 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile (1b, 500 mg, 2 mmol) was added to a solution of potassiumhydroxide (560 mg, 10 mmol) in ethylene glycol/water (20 ml/10 ml), the reaction solution was heated to 100°C and kept overnight. TLC test found that the raw materials disappeared,the reaction solution was cooled to roomtemperature, diluted with water (20 ml), and adjusted to pH = 3-4 with hydrochloric acid, extracted with ethyl acetate(40ml 3 3), the organic phases were combined, washed with water (50 ml), and washed with saturated saline (50 ml),dried with anhydrous sodium sulfate, and concentrated to give the yellow oily compound 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetic acid (19a, 320 mg), with a yield of 60%
With sulfuric acid In lithium hydroxide monohydrate at 10 - 50℃; for 1h; 3-1.1 Step 1: Add E2 (20g, CAS NO.1401031-37-5) and 80mL of water to a 250mL three-necked flask, cool down to 10-15°C, stir, drop in sulfuric acid solution (configured by adding 11.5g concentrated sulfuric acid to 20mL water) After dropping, the temperature was raised to 45-50°C, and the temperature was kept stirring for 1 hour.The temperature was lowered to 5-10° C., 100 mL of toluene was added, 30 g of 20% sodium hydroxide solution was added dropwise, and the mixture was stirred at room temperature for 1 hour after the dropping.The organic phase was separated and the aqueous phase was extracted twice with 2×100 mL of toluene. The organic phases were combined, washed once with 100 mL of saturated brine, dried over anhydrous sodium sulfate, filtered, and put into the next step with toluene solution.
  • 46
  • [ CAS Unavailable ]
  • [ 1401031-37-5 ]
YieldReaction ConditionsOperation in experiment
80% With potassium hydroxide In ethylene glycol at 120℃; for 3h; 1.5 Step 5: Preparing 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile (1b) 2-cyano-2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-ylidene]ethyl acetate (1a, 0.66 g, 2 mmol) was added intoa pre-dissolved solution of the potassium hydroxide (112 mg, 2 mmol) in ethylene glycol (5 ml). The mixture was heatedto 120°C and reacted for 3 hours, then cooled down. Water (50 ml) was added, the system was extracted with diethylether (3350 ml), washed with water (50 ml), dried with anhydrous magnesium sulfate, filtered and concentrated, andpurified by column chromatography (developing solvent was 5% to 40% ethyl acetate/n-hexane) to obtain 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile (1b, 400 mg), with a yield of: 80%
  • 47
  • [ 1401031-37-5 ]
  • [ 917-54-4 ]
  • [ 2300115-57-3 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile; methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h; Stage #2: With palladium 10% on activated carbon; hydrogen In methanol at 20℃; 27.1 Step 1: Preparing 1-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl) propan-2-amine (27a) 2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile (1b, 0.256 g, 1 mmol) was dissolved in anhydrous tetrahydrofuran(10 mL) and cooled to -78°C, methyllithium (0.94 ml, 1.5 mmol, 1.6 M of diethyl ether solution) was slowlyadded dropwise thereto. After the addition, the reaction was continued for one hour at -78°C, and quenched by slowlyadding methanol (10 ml), then slowly warmed to room temperature and continued stirring for 2 hours. The reactionsolution was quenched by adding ice water (10 mL), and extracted with ethyl acetate (15 mL 3 3), the organic layerwas washed with water (15 mL 33) and then with saturated sodium chloride (15 mL), dried and concentrated. Theconcentrated reaction solution was dissolved by adding methanol, and 10% palladium carbon (10 mg) was added,hydrogen was inlet, and the reaction was conducted at room temperature overnight. After filtration, the solvent wasevaporated to dryness to obtain 1-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl) propan-2-amine (27a) as a yellow oilysubstance (27a, 0.15 g), with a yield of 55%, which was used without further purification
  • 48
  • [ 1401031-37-5 ]
  • [ 2792722-67-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid / lithium hydroxide monohydrate / 1 h / 10 - 50 °C 2: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / 0 - 45 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: sulfuric acid / lithium hydroxide monohydrate / 1 h / 10 - 50 °C 2: dichlorosulfoxide / 3 h / 5 - 55 °C / Inert atmosphere 3: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1.5 h / 0 - 45 °C / Inert atmosphere
  • 49
  • [ 1401031-37-5 ]
  • [ 2792722-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sulfuric acid / lithium hydroxide monohydrate / 1 h / 10 - 50 °C 2: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / 0 - 45 °C / Inert atmosphere 3: 1,1'-binaphthyl-2,2'-dihydrogen phosphate / tetrahydrofuran / 1 h / 20 °C
Multi-step reaction with 4 steps 1: sulfuric acid / lithium hydroxide monohydrate / 1 h / 10 - 50 °C 2: dichlorosulfoxide / 3 h / 5 - 55 °C / Inert atmosphere 3: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1.5 h / 0 - 45 °C / Inert atmosphere 4: 1,1'-binaphthyl-2,2'-dihydrogen phosphate / tetrahydrofuran / 1 h / 20 °C
  • 50
  • [ 1401031-37-5 ]
  • [ 2667632-87-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfuric acid / lithium hydroxide monohydrate / 1 h / 10 - 50 °C 2: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / 0 - 45 °C / Inert atmosphere 3: 1,1'-binaphthyl-2,2'-dihydrogen phosphate / tetrahydrofuran / 1 h / 20 °C 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C 5: triethylamine; sodium tris(acetoxy)borohydride / ethanol / 2 h / 10 - 15 °C / Large scale
Multi-step reaction with 5 steps 1: sulfuric acid / lithium hydroxide monohydrate / 1 h / 10 - 50 °C 2: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / 0 - 45 °C / Inert atmosphere 3: 1,1'-binaphthyl-2,2'-dihydrogen phosphate / tetrahydrofuran / 1 h / 20 °C 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C 5: sodium cyanotrihydridoborate / methanol / 3 h / 20 °C
Multi-step reaction with 6 steps 1: sulfuric acid / lithium hydroxide monohydrate / 1 h / 10 - 50 °C 2: dichlorosulfoxide / 3 h / 5 - 55 °C / Inert atmosphere 3: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1.5 h / 0 - 45 °C / Inert atmosphere 4: 1,1'-binaphthyl-2,2'-dihydrogen phosphate / tetrahydrofuran / 1 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C 6: triethylamine; sodium tris(acetoxy)borohydride / ethanol / 2 h / 10 - 15 °C / Large scale
Multi-step reaction with 6 steps 1: sulfuric acid / lithium hydroxide monohydrate / 1 h / 10 - 50 °C 2: dichlorosulfoxide / 3 h / 5 - 55 °C / Inert atmosphere 3: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1.5 h / 0 - 45 °C / Inert atmosphere 4: 1,1'-binaphthyl-2,2'-dihydrogen phosphate / tetrahydrofuran / 1 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C 6: sodium cyanotrihydridoborate / methanol / 3 h / 20 °C

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