3-Pyrrolidinol, hydrochloride (1:1), (3R)-
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3-Pyrrolidinol, hydrochloride (1:1), (3R)-
structure -
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CAS No:
104706-47-0
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Formula:
C4H9NO.ClH
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Chemical Name:
3-Pyrrolidinol, hydrochloride (1:1), (3R)-
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Synonyms:
3-Pyrrolidinol,hydrochloride (1:1),(3R)-;3-Pyrrolidinol,hydrochloride,(R)-;3-Pyrrolidinol,hydrochloride,(3R)-;(R)-(-)-3-Pyrrolidinol hydrochloride;(R)-(-)-3-Hydroxypyrrolidine hydrochloride;(3R)-3-Hydroxypyrrolidine hydrochloride;(3R)-3-Pyrrolidinol hydrochloride;(R)-3-Hydroxypyrrolidine hydrochloride;(R)-3-Pyrrolidinol hydrochloride;3-(R)-Hydroxypyrrolidine hydrochloride;(R)-Pyrrolidin-3-ol hydrochloride;(3R)-Pyrrolidin-3-ol hydrochloride;(R)-(-)-3-Hydroxypyrrolidine hydrochloride;(R)-3-Hydroxypyrrolidine hydrochloride
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CAS No:
3-Pyrrolidinol, hydrochloride (1:1), (3R)- Basic Attributes
123.58
123.045090
1592732-453-0
DTXSID90374747
29339900
Characteristics
32.3
0.47140
106-109 °C @ Solvent: Acetone
224.7ºC at 760 mmHg
-7.8 ° (C=3.5, MeOH)
Soluble in DMSO.
Room temperature.
Safety Information
NONH for all modes of transport
3
36/37/38-41-38-37
26-36-38
Xi
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
3-Pyrrolidinol, hydrochloride (1:1), (3R)- Use and Manufacturing
PREPARATION OF 3-(R)-(-)-HYDROXYPYRROLIDINE HYDROCHLORIDE (FORMULA VII); Cyclohexanol (80 liters) were taken into a reactor and heated to about 155 Step 1; Preparation of 3-(R)-hydroxypyrrolidine hydrochloride (VIII): To a stirred suspension of commercially available (25, 4i?)-4-hydroxy-2- pyrrolidinecarboxylic acid (L-hydroxyproline) (VII) (100 g, 0.762 mol) in anhydrous cyclohexanol (500 ml), was added 2-cyclohexen-l-one (5 ml). The resulting mixture was heated under reflux at about 154°C for about 48 hour. The obtained clear solution was allowed to cool to room temperature and then was cooled further to 10°C. To this, about 15 percent solution of hydrochloric acid in ethanol (234 ml) was added and then stirred for 30 minutes. The separated solid was filtered under suction and washed with ethyl acetate (2 x 100 ml). The solid was dried under reduced pressure to obtain 47.5 g of 3-(R)- hydroxypyrrolidine hydrochloride (VIII) in 51 percent yield. The solid was used without further purification in the next step. Analysis: Mass: 87.8 (M+l) as free base; for Molecular weight of 123.57 and Molecular Formula of CThe compound trans-4-hydroxy-L-proline (10.0 g, 76.3 mM) was taken in a mixture of anhydrous cyclohexanol (50.0 ml) and 2-cyclohexen-l-one (0.5 ml). The reaction mixture was heated at 155-160°C for about 11 hours. To the reaction mixture, ethanolic hydrochloric acid (70.0 ml) was added with constant stirring, and kept at 0-5°C overnight. The separated solid was filtered under nitrogen atmosphere, washed with ethyl acetate (10.0 ml) and dried under vacuum to get the title compound. Yield = 35percent (3.3 g, 26.7 MM). 1H NMR (DMSO-d6): δ 9.57 (brs, 1H), 9.33 (brs, 1H), 5.00-5.75 (brs, 1H), 4.38 (s, 1H), 3.01-3.47 (M, 4H), 1.84-1.92 (M, 2H)(R)-tert-Butyl 3-hydroxypyrrolidine-1 -carboxylate (250 mg, 1.34 mmol) was dissolved inHCI/dioxane (4 M, 5 mL) and stirred at rt for 1 h. The reaction mixture was concentrated to give the title compound (150 mg, yield 90percent) as a white solid.1H NMR (300 MHz, DMSO-d6): 6 9.47 (br s, I H), 9.24 (br 5, 1 H), 4.38 (s, 1 H), 3.57-2.96 (m, 4H), 1.95-1.79 (m, 2H).N-(Tert-butoxycarbonyl)-(R)-3-pyrrolidinol (5g; 26.70 mmol) was diluted in 15 ml of methanol and 5 ml of HCl37percent were added. The reaction mixture was stirred at room temperature overnight, then it was concentrated in vacuo.2.1 g (17.07 mmol; 63percent) of the desired product were obtained as hydrochloride.2-Chloro-5-trifluoromethylpyridine (viii) (90.9 g, 0.5 mol), ethanol (200 mL), 3(R)-hydroxypyrrolidine hydrochloride, (vii) (61.8 g, 0.5 mol), potassium carbonate (82.9 g, 0.6 mol) and water (50 mL) were charged to a reactor vessel.
(R)-(-)-3-Hydroxypyrrolidine is a chiral hydroxy derivative of pyrrlodine used in the preparation of chiral niologically active compounds such as muscarinic receptor antagonists and antimicrobial agents.
Computed Properties
Molecular Weight:123.58
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:2
Exact Mass:123.0450916
Monoisotopic Mass:123.0450916
Topological Polar Surface Area:32.3
Heavy Atom Count:7
Complexity:46.8
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
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3-Pyrrolidinol, hydrochloride (1:1), (3R)-
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