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Chemical Structure| 1221280-93-8 Chemical Structure| 1221280-93-8

Structure of 1221280-93-8

Chemical Structure| 1221280-93-8

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Product Details of [ 1221280-93-8 ]

CAS No. :1221280-93-8
Formula : C10H19NO5S
M.W : 265.33
SMILES Code : CS(=O)(OC1CC(NC(OC(C)(C)C)=O)C1)=O

Safety of [ 1221280-93-8 ]

Application In Synthesis of [ 1221280-93-8 ]

* 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 [ 1221280-93-8 ]

[ 1221280-93-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1221280-93-8 ]
  • [ 35344-95-7 ]
  • tert-butyl N-[trans-3-(4-formyl-1H-pyrazol-1-yl)cyclobutyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h; 1H- <strong>[35344-95-7]pyrazole-4-carbaldehyde</strong> (1.73 g, 18.00 mmol, 1.20 eq.) and Cs2CO3 (9.78 g, 30.02 mmol, 2.00 eq.) were added to a solution of tert-butyl N-[3-(methanesulfonyloxy)cyclobutyl]carbamate (4 g, 15.08 mmol, 1.00 eq.) in DMF (100 mL). The resulting solution was stirred for 16 hours at 80 C and then diluted with 300 mL of water. The resulting solution was extracted with ethyl acetate (3x300 mL) and the organic layers combined. The resulting mixture was washed with brine (3x500 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Flash with the following conditions: Column, C18 silica gel; mobile phase, X:H20 Y:ACN=70/30 increasing to X:H20 Y:ACN=20/80 within 30 mm;Detector, UV 254 nm. The isomers were separated by Prep-SFC with the following conditions (Prep SFC8O-2): Column, Chiralpak TB, 2*25cm, 5um; mobile phase, CO2 (80%), IPA (20%); Detector, UV 220nm. This resulted in 1.2 g (30%) of tert-butyl N-trans-3-(4-formyl-1H- pyrazol-1-yl)cyclobutyl]carbamate as a white solid.
  • 2
  • [ 1221280-93-8 ]
  • [ 35344-95-7 ]
  • tert-butyl N-[cis-3-(4-formyl-1H-pyrazol-1-yl)cyclobutyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 4h; into a 100-mL round-bottom flask, was placed a solution of tert-butyl N-[3-(methanesulfonyloxy)cyclobutyl]carbamate (2.65 g, 9.99 mmol, 1.00 eq.), <strong>[35344-95-7]1H-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong></strong> (1.152 g, 11.99 mmol, 1.20 eq.) and Cs2CO3 (6.52 g, 20.01 mmol, 2.00 eq.) inDMF (20 mL). The resulting solution was stirred for 4 h at room temperature. The reaction was then quenched by the addition of 100 mL of water. The resulting solution was extracted with 3x100 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 100 mL of brine. The mixture was dried over anhydrous sodium sulfate andconcentrated under vacuum. The crude product was purified by Flash-Prep-HPLC with the following conditions (CombiFlash-1): Column, C18 silica gel; mobile phase, MeCN/H20=60:40 increasing to MeCN/H20=70:30 within 3 mm; Detector, UV 254 nm. The crude product was purified by Prep-SFC with the following conditions (prep SFC 350-2):Column: Phenomenex Lux 5u Cellulose-4 250*50mm; mobile Phase A: C02:70, Mobile PhaseB: MeQH-HPLC:30; Flow rate: 150 mL/min; 254 nm; RT1:4.53; RT2:5.36. This resulted in 712 mg (54%) of tert-butyl N-[cis-3 -(4-formyl- 1 H-pyrazol- 1 -yl)cyclobutyl]carbamate as a white solid.
  • 3
  • [ 1221280-93-8 ]
  • [ 35344-95-7 ]
  • tert-butyl N-trans-[3-(4-formyl-1H-pyrazol-1-yl)cyclobutyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h; Step 3: tert-butyl Af-fra is-3-(4-formyI-lH-pyrazo -yl)cyclobutyl]carbamate: l H-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong> (1.73 g, 18.00 mmol, 1.20 eq.) and Cs2C03 (9.78 g, 30.02 mmol, 2.00 eq.) were added to a solution of tert-butyl N-[3- (methanesulfonyloxy)cyclobutyl]carbamate (4 g, 15.08 mmol, 1.00 eq.) in DMF (100 mL). The resulting solution was stirred for 16 hours at 80 C and then diluted with 300 mL of water. The resulting solution was extracted with ethyl acetate (3x300 mL) and the organic layers combined. The resulting mixture was washed with brine (3x500 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Flash with the following conditions: Column, CI 8 silica gel; mobile phase, X:H20 Y:ACN=70/30 increasing to X:H20 Y:ACN=20/80 within 30 min; Detector, UV 254 nm. The isomers were separated by Prep-SFC with the following conditions (Prep SFC80-2): Column, Chiralpak IB, 2*25cm, 5um; mobile phase, CO2(80%), IPA(20%); Detector, UV 220nm. This resulted in 1.2 g (30%) of tert-butyl N-/ra5-3-(4-formyl-lH-pyrazol-l -yl)cyclobutyl]carbamate as a white solid.
30% With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h; lH-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong> (1.73 g, 18.00 mmol, 1.20 eq.) and Cs2C03 (9.78 g, 30.02 mmol, 2.00 eq.) were added to a solution of tert-butyl N-[3- (methanesulfonyloxy)cyclobutyl]carbamate (4 g, 15.08 mmol, 1.00 eq.) in DMF (100 mL). The resulting solution was stirred for 16 hours at 80 C and then diluted with 300 mL of water. The resulting solution was extracted with ethyl acetate (3x300 mL) and the organic layers combined. The resulting mixture was washed with brine (3x500 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Flash with the following conditions: Column, CI 8 silica gel; mobile phase, X:H20 Y:ACN=70/30 increasing to X:H20 Y:ACN=20/80 within 30 min; Detector, UV 254 nm. The isomers were separated by Prep-SFC with the following conditions (Prep SFC80-2): Column, Chiralpak IB, 2*25cm, 5um; mobile phase, C02 (80%), IPA (20%); Detector, UV 220nm. This resulted in 1.2 g (30%) of tert-butyl N-fra ,-3-(4-formyl-lH-pyrazol-l-yl)cyclobutyl]carbamate as a white solid.
30% With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h; lH-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong> (1.73 g, 18.00 mmol, 1.20 eq.) and Cs2C03 (9.78 g, 30.02 mmol, 2.00 eq.) were added to a solution of tert-butyl N-[3-(methanesulfonyloxy)cyclobutyl] carbamate (4 g, 15.08 mmol, 1.00 eq.) in DMF (100 mL). The resulting solution was stirred for 16 hours at 80 C and then diluted with 300 mL of water. The resulting solution was extracted with ethyl acetate (3x300 mL) and the organic layers combined. The resulting mixture was washed with brine (3x500 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Flash with the following conditions: Column, C18 silica gel; mobile phase, X:H20 Y:ACN=70/30 increasing to X:H20 Y:ACN=20/80 within 30 min; Detector, UV 254 nm. The isomers were separated by Prep-SFC with the following conditions (Prep SFC80-2): Column, Chiralpak IB, 2*25cm, 5um; mobile phase, CO2 (80%), IPA (20%); Detector, UV 220nm. This resulted in 1.2 g (30%) of tert-butyl N-trans-3-(4- formyl-lH-pyrazol-l-yl)cyclobutyl] carbamate as a white solid.
  • 4
  • [ 1221280-93-8 ]
  • [ 35344-95-7 ]
  • tert-butyl N-[cis-3-(4-formyl-1H-pyrazol-1-yl)cyclobutyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 4h; into a 100-mL round-bottom flask, was placed a solution of tert-butyl N-[3- (methanesulfonyloxy)cyclobutyl]carbamate (2.65 g, 9.99 mmol, 1.00 eq.), lH-pyrazole-4- carbaldehyde (1.152 g, 11.99 mmol, 1.20 eq.) and Cs2C03 (6.52 g, 20.01 mmol, 2.00 eq.) in DMF (20 mL). The resulting solution was stirred for 4 h at room temperature. The reaction was then quenched by the addition of 100 mL of water. The resulting solution was extracted with 3x100 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 100 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Flash-Prep-HPLC with the following conditions (CombiFlash-1): Column, CI 8 silica gel; mobile phase, MeCN/H2O=60:40 increasing to MeCN/H2O=70:30 within 3 min; Detector, UV 254 nm. The crude product was purified by Prep-SFC with the following conditions (prep SFC 350-2): Column: Phenomenex Lux 5u Cellulose-4 250*50mm; mobile Phase A: CO2:70, Mobile Phase B: MeOH-HPLC:30; Flow rate: 150 mL/min; 254 nm; RTL4.53; RT2:5.36. This resulted in 712 mg (54%) of tert-butyl N-[cw-3-(4-formyl-lH-pyrazol-l-yl)cyclobutyl]carbamate as a white solid.
54% With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 4h; into a 100-mL round-bottom flask, was placed a solution of tert-butyl N-[3- (methanesulfonyloxy)cyclobutyl]carbamate (2.65 g, 9.99 mmol, 1.00 eq.), lH-pyrazole-4- carbaldehyde (1.152 g, 11.99 mmol, 1.20 eq.) and Cs2C03 (6.52 g, 20.01 mmol, 2.00 eq.) in DMF (20 mL). The resulting solution was stirred for 4 h at room temperature. The reaction was then quenched by the addition of 100 mL of water. The resulting solution was extracted with 3x100 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 100 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Flash-Prep-HPLC with the following conditions (CombiFlash-1): Column, CI 8 silica gel; mobile phase, MeCN/H2O=60:40 increasing to MeCN/H2O=70:30 within 3 min; Detector, UV 254 nm. The crude product was purified by Prep-SFC with the following conditions (prep SFC 350-2): Column: Phenomenex Lux 5u Cellulose-4 250*50mm; mobile Phase A: CO2:70, Mobile Phase B: MeOH-HPLC:30; Flow rate: 150 mL/min; 254 nm; RTL4.53; RT2:5.36. This resulted in 712 mg (54%) of tert-butyl N-[cw-3-(4-formyl-lH-pyrazol-l-yl)cyclobutyl]carbamate as a white solid.
 

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