| Identification | Back Directory | [Name]
3-Hydroxymethylpyrrolidine | [CAS]
5082-74-6 | [Synonyms]
Albb-005836
AKOS BB-9752
DL-beta-Prolinol
DL-^b-Prolinol, 97+%
3-Pyrrolidinemethanol
3-pyrrolidinylmethanol
PYRROLIDIN-3-YL-METHANOL
ASINEX-REAG BAS 10144565
PYRROLIDINE-3-YL METHANOL
3-Hydroxymethylpyrrolidine
3-HYDROXYMETHYL-PYRROLIDIN
(RS)-3-Pyrrolidinemethanol
pyrrolidin-3-ylMethanol HCl
(RS)-3-(Hydroxymethyl)pyrrolidine
pyrrolidin-3-ylmethanol hydrochloride
pyrrolidin-3-ylmethanol(SALTDATA: FREE) | [Molecular Formula]
C5H11NO | [MDL Number]
MFCD07773080 | [MOL File]
5082-74-6.mol | [Molecular Weight]
101.15 |
| Chemical Properties | Back Directory | [Boiling point ]
165-171℃ | [density ]
0.979 | [Fp ]
86℃ | [storage temp. ]
2-8°C | [pka]
14.93±0.10(Predicted) | [Appearance]
Colorless to light yellow Liquid | [Water Solubility ]
Slightly soluble in water | [Sensitive ]
Hygroscopic | [BRN ]
1420904 | [InChI]
InChI=1S/C5H11NO/c7-4-5-1-2-6-3-5/h5-7H,1-4H2 | [InChIKey]
QOTUIIJRVXKSJU-UHFFFAOYSA-N | [SMILES]
N1CCC(CO)C1 |
| Hazard Information | Back Directory | [Uses]
3-?Pyrrolidinemethanoln is a useful reagent in preparation of orally active (heterocyclic aminomethyl)pyrazoloquinolines as potent PDE10 inhibitors for the management of schizophrenia. | [Synthesis]
The general procedure for the synthesis of 3-pyrrolidinemethanol from methyl 5-oxopyrrolidine-3-carboxylate is as follows: 2 kg of methyl 5-oxo-3-pyrrolidinecarboxylate is dissolved in 20 liters of tetrahydrofuran, and 1.9 kg of sodium borohydride is added in batches at room temperature. Subsequently, 3.9 kg of boron trifluoride ether solution was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was stirred at room temperature for 10 minutes and then heated to reflux for about 4 hours. Upon completion of the reaction, the reaction was quenched with water and extracted with ethyl acetate. The organic phases were combined and concentrated to give a light yellow oily liquid. This oily liquid was dissolved in ethanol, 500 g of sodium borohydride was added and heated to reflux for 2 hours. At the end of the reaction, the reaction was again quenched with water and extracted with ethyl acetate. The organic phase was washed sequentially with saturated aqueous sodium bicarbonate and saturated brine, and finally the organic phase was concentrated to give 1.2 kg of 3-pyrrolidinemethanol in 86% yield. | [References]
[1] Patent: CN106588738, 2017, A. Location in patent: Paragraph 0032; 0034; 0039; 0042; 0044 |
|
|