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CAS No. : | 158261-95-1 | MDL No. : | MFCD09864547 |
Formula : | C8H17NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FKCMGWYAPOCAKE-UHFFFAOYSA-N |
M.W : | 143.23 | Pubchem ID : | 10012019 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Intermediate 25: 3-Pyrrolidin-1-yl-butan-1-ol; [] Pyrrolidine (28.15g, 0.4mol), toluene (200ml), catalytic p-TsOH (200mg) and ethyl acetoacetate (20g, 0.15mol) were refluxed together in a Dean-Stark apparatus under N2 for 3hours. The reaction was cooled to room temperature and concentrated in vacuo. NaBH4 (3.1 g, 82mmol) was dissolved in MeOH (50ml) and cooled to 0-5C. A portion of the previous crude reaction (5g, 27mmol) in MeOH (25ml) was added to the reaction mixture and stirred for 72hours. The reaction was quenched with an aqueous solution of NaOH (1%w/w, 50ml) and concentrated in vacuo. The aqueous phase was extracted with TBME (3 x 50ml). The combined organic extracts were dried over MgSO4, filtered, washed with TBME and concentrated in vacuo to give a mixture of the title compound, 3-pyrrolidin-1-yl-butanoic acid ethyl ester and residual TBME (3.5g). The mixture (3.5g) in THF (20ml) was added to a solution of LiALH4 (1 M in THF, 33.5ml, 33.5mmol) at 0-5C under N2. The reaction was allowed to warm to room temperature and stirred for 3hours. The reaction was quenched with an aqueous solution of NaOH (1%w/w, 50ml) at 0-5C, filtered and washed with THF (3 x 20ml). The combined organic layers were dried over MgSO4, filtered, washed with THF and concentrated in vacuo to give the title compound as a yellow oil (2g, 73%th).1H NMR (400MHz, CDCl3) δ5.98 (br s, 1 H), 3.90 (ddd, 1 H), 3.77 (ddd, 1 H), 2.90 (m, 1 H), 2.70-2.55 (m, 4H), 1.80-1.56 (m, 6H), 1.09 (d, 3H).; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With thionyl chloride; In dichloromethane; at 0 - 20℃; | Step 2:; 3-Pyrrolidin-1-yl-butan-1-ol (1.0g, 7mmol) was dissolved in DCM (20ml). The reaction was cooled to 0-5C and thionyl chloride (1.65g, 14mmol) was added slowly. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was concentrated in vacuo and azeo-dried with DCM (20ml) to give the title compound (1.4g, 100%th) as a brown oil.1H NMR (400MHz, CDCl3) δ12.45 (br s, 1 H), 3.84-3.71 (m, 3H), 3.56 (m, 1H), 3.38 (m, 1 H), 2.92-2.79 (m, 2H), 2.45-1.99 (m, 6H), 1.51 (d, 3H). |
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