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CAS No. : | 144043-17-4 | MDL No. : | MFCD00191309 |
Formula : | C12H18N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UEAYAIWNQQWSBK-GFCCVEGCSA-N |
M.W : | 190.28 | Pubchem ID : | 10035441 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
98.6% | With lithium aluminium tetrahydride In tetrahydrofuran at -40℃; for 4 h; Reflux | A tert-butyl (R)-(1-benzylpyrrolidin-3-yl)carbamate 2aa (3.20g, 11.6mmol) solution in 58.0mL of 61 tetrahydrofuran was placed in a 100mL round-bottom flask. After it was cooled at −40°C, 62 lithium aluminum hydride (2.64g, 69.6mmol) was slowly added to the stirred mixture. The reaction mixture was refluxed for 4h and then cooled down to −40°C. The reaction was quenched with 2.70mL of deionized 46 water, 2.70mL of 15percent 63 sodium hydroxide solution, and 8.10mL of deionized water. Then, Celite 545 was added and the mixture was stirred for 30min before being filtered through a Celite 545 pad. The filtered solution was concentrated under reduced pressure and the residue was extracted with dichloromethane three times. Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with flash column chromatography (methanol: dichloromethane: ammonium hydroxide=5:90:5). Removing the solvent in vacuo provided 2.17g of 64 (R)-1-benzyl-N-methylpyrrolidin-3-amine (98.6percent yield). 1H NMR (400MHz, CDCl3) δ 7.34–7.24 (m, 5H), 3.62 (s, 2H), 3.25–3.19 (m, 1H), 2.74 (dd, J=9.4, 6.8Hz, 1H), 2.64 (dt, J=8.6, 6.0Hz, 1H), 2.52 (dt, J=8.4, 6.0Hz, 1H), 2.41–2.37 (m, 1H), 2.38 (s, 3H), 2.19–2.09 (m, 1H), 2.02 (bs, 1H), 1.63–1.56 (m, 1H). |
0.98% | With lithium aluminium tetrahydride In tetrahydrofuranReflux | After 3.204 g of tert-butyl (R)-(1-benzylpyrrolidine-3-yl)carbamate was added to a 100-mL round-bottomed flask, 58.0 mL of tetrahydrofuran and 2.639 g of lithium aluminum hydride (LiAlH4) were sequentially added thereto. The reaction mixture was refluxed overnight and then cooled at 0°C. 2.7 mL of deionized water was slowly added to the reaction mixture while cooling. After the reaction mixture was stirred for about 5 minutes, 2.7 mL of a 15percent sodium hydroxide (NaOH) aqueous solution was added thereto. The reaction mixture was further stirred for about 5 minutes, and then 8.1 mL of deionized water was added thereto to terminate the reaction. The reaction mixture was filtered through a Celite™ 545 filter agent (available from DAEJUNG Chemicals & Metals Co., Ltd.).The resulting filtrate was concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (MeOH:CH2Cl2:NH4OH=5:90:5). As a result, 2.174 g of (R)-1-benzyl-N-methylpyrrolidine-3-amine was obtained with a yield of about 98.6percent. (0088) 1H NMR (400 MHz, CDCl3) δ7.34-7.24 (m, 5H), 3.62 (s, 2H), 3.25-3.19 (m, 1H), 2.74 (dd, J = 9.4, 6.8 Hz, 1H), 2.64 (dt, J = 8.6, 6.0 Hz, 1H), 2.52 (dt, J = 8.4, 6.0 Hz, 1H), 2.41-2.37 (m, 1H), 2.38 (s, 3H), 2.19-2.09 (m, 1H), 2.02 (bs, 1H), 1.63-1.56 (m, 1H). |
A427823[ N/A ]
(R)-1-Benzyl-N-methylpyrrolidin-3-amine dihydrochloride
Reason: Free-salt
A483651[ 169749-99-9 ]
(S)-N-Benzyl-3-methylaminopyrrolidine
Reason: Optical isomers