[ CAS No. 6435-78-5 ] {[proInfo.proName]}

Name: 6435-78-5|1-Tosylpyrrolidine|97%
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SKU: A291315
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 6435-78-5 ]

CAS No. :	6435-78-5	MDL No. :	MFCD00455022
Formula :	C₁₁H₁₅NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KDWPQSBXEHQMSD-UHFFFAOYSA-N
M.W :	225.31	Pubchem ID :	247206
Synonyms :

Safety of [ 6435-78-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302-H317	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6435-78-5 ]

* 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.

Upstream synthesis route of [ 6435-78-5 ]
Downstream synthetic route of [ 6435-78-5 ]

[ 6435-78-5 ] Synthesis Path-Upstream 1~1

1
[ 78521-69-4 ]
[ 13124-15-7 ]
[ 6435-78-5 ]

Reference： [1] Journal of Organic Chemistry, 2018, vol. 83, # 8, p. 4712 - 4729

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Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine In chloroform at 0 - 20℃; for 19h;
92%	With tert.-butylhydroperoxide; ammonium iodide In tetrahydrofuran at 80℃; for 15h; Sealed tube;	4 Example 4:Synthesis of 1-toluenesulfonylpyrrolidine Substrate 57.2 mg (0.3 mmol)4-methylbenzenesulfonyl chloride and 42.7 mg (0.6 mmol) of tetrahydropyrrole,Catalyst 4.34 mg (0.03 mmol) ammonium iodide, 0.12 mLAdd tert-butyl hydroperoxide and 2 mL of THF to a 30 mL sealed tube under air.The tube was then placed in an 80 ° C oil bath for 15 h. After the reaction,The reaction solution was cooled to room temperature, and 40 mL of saturated brine was added.It was extracted three times with 100 mL of ethyl acetate and the organic layers were combined.The organic layer was dried over anhydrous sodium sulfate and filtered.The filtrate was distilled under reduced pressure and separated by silica gel column chromatography.(ethyl acetate / petroleum ether: 1/2 as eluent),Got 101.8mg white solid,The yield was 92%.
86%	With triethylamine In dichloromethane at 20℃; for 16h;	1 Example 1 : Compound 3aa: preparation of 1 -tosylpyrrolidine To a solution of 4-methylbenzenesulfonyl chloride (217 mg, 1 .14 mmol, 1 eq) in methylene chloride (10 ml_) were added pyrrolidine (121 .4 mg, 0.14 ml_, 1 .71 mmol, 1 .5 eq) and triethylamine (172.8 mg, 0.24 ml_, 1 .71 mmol, 1 .5 eq). The mixture was stirred during 16 h, hydrolyzed with an aqueous solution of HCI (2M) and extracted with methylene chloride. The organic layer was washed with water, dried over MgS04, filtrated and evaporated under vacuum. The crude product was purified by column chromatography (Si02, petroleum ether/EtOAc: 6/4) to afford the product as a white solid in 86% yield. (0129) mp: 129°C (0130) 1H NMR (300 MHz, CDCI3): d 7.71 (d, 2H, 8.1 Hz, H2 and H6); 7.31 (d, 2H, 8.1 Hz, H3 and H5); 3.25-3.20 (m, 4H, H2· a, H2· b, H5 ,a and H5 ,P); 2.43 (s, 3H, CH3); 1 .76-1 .72 (m, 4H, H3·,a, H3·,b, H4·,a and H4·,b). (0131) 13C NMR (75 MHz, CDCI3): d 143.3 (C4); 133.9 (C^; 129.6 (2C, C3 and C5); 127.6 (2C, C2 and C6); 47.9 (2C, C2· and C5); 25.2 (2C, C3· and C4); 21 .5 (CH3). (0132) MS: ESI+: [M+H]+ = 226.1 ; [M+Na]+ = 248.0. (0133) HRMS (ESI+) calculated for Cn H15NNa02S [M+Na+] m/z = 248.0721 found 248.0726. (0134) IR ATR: v (cm 1) 3092.45-3035.04 (=C-H); 2975.45-2866.37 (-C-H); 1330.87 (S02, as); 1 105.81 (S02,s).

	With sodium hydroxide; diethyl ether
	With α-picoline
45 mg	In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: toluene-4-sulfonamide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; for 1h;
	With potassium hydroxide; ethanol Kochen;

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hypochlorite In water Ambient temperature;
95%	With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water; acetonitrile at 50℃; for 8h;
95%	With ammonium bromide In water; acetonitrile Electrolysis;

[ CAS No. 6435-78-5 ] {[proInfo.proName]}

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[ 6435-78-5 ] Synthesis Path-Upstream 1~1

[ 6435-78-5 ] Synthesis Path-Downstream 1~88