[ CAS No. 100243-39-8 ] {[proInfo.proName]}

Name: 100243-39-8|(S)-Pyrrolidin-3-ol|97%
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SKU: A175317
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Quality Control of [ 100243-39-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 100243-39-8 ]

SDS Specification

Alternatived Products of [ 100243-39-8 ]

Product Details of [ 100243-39-8 ]

CAS No. :	100243-39-8	MDL No. :	MFCD00192426
Formula :	C₄H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JHHZLHWJQPUNKB-BYPYZUCNSA-N
M.W :	87.12	Pubchem ID :	2733874
Synonyms :

Calculated chemistry of [ 100243-39-8 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	27.11
TPSA :	32.26 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.2
Log Po/w (XLOGP3) :	-0.69
Log Po/w (WLOGP) :	-1.04
Log Po/w (MLOGP) :	-0.57
Log Po/w (SILICOS-IT) :	0.52
Consensus Log Po/w :	-0.12

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.05
Solubility :	98.8 mg/ml ; 1.13 mol/l
Class :	Highly soluble
Log S (Ali) :	0.49
Solubility :	268.0 mg/ml ; 3.07 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.13
Solubility :	64.4 mg/ml ; 0.74 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.25

Safety of [ 100243-39-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 100243-39-8 ]

* 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 [ 100243-39-8 ]
Downstream synthetic route of [ 100243-39-8 ]

[ 100243-39-8 ] Synthesis Path-Upstream 1~5

1
[ 101469-91-4 ]
[ 40499-83-0 ]
[ 100243-39-8 ]

Reference： [1] Synthetic Communications, 1985, vol. 15, # 7, p. 587 - 598

2
[ 501-53-1 ]
[ 100243-39-8 ]
[ 100858-32-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine In dichloromethane at 5 - 20℃; for 48 h;	Step 1: preparation of benzyl (3S)-3-hydroxypyrrolidine-1-carboxylate. A solution of (3S)-pyrrolidin-3-ol (10.0 g, 0.12 mol) in dichloromethane (130 mL) was cooled to 5°C. Triethylamine (16.9 mL, 0.12 mol) was added, followed by drop wise addition ofbenzyl chloroformate (13.9 mL, 0.10 mol), ensuring that the temperature did not exceed5°C. The reaction mixture was then allowed to stir at ambient temperature for 48h, after which it was poured into aqueous saturated sodium bicarbonate and extracted into dichloromethane. The combined organic layers were washed with aqueous saturated sodium bicarbonate, dried over magnesium sulfate, and concentrated in vacuo. The resulting crude oil was purified by silica gel column chromatography (50percent ether hexanes followed by ether) to afford the title compound as a clear oil (14 g, 92percent).

Reference： [1] Patent: WO2014/68527, 2014, A1, . Location in patent: Page/Page column 81; 82
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 13, p. 1773 - 1778

3
[ 624-28-2 ]
[ 100243-39-8 ]
[ 946002-90-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium carbonate In <i>tert</i>-butyl alcohol at 140℃; for 3 h;	To a stirred solution of 2,5-dibromopyridine (1.0 g, 4.2 mmol) in tert-butanol (5 ml) was added (S)-3-hydroxypyrrolidine (0.74 g, 8.44 mmol; Aldrich) and sodium carbonate (1.34 g, 12.70 mmol). The mixture was heated at 140° C. for 3 hours in a reacti-vial. After cooling to room temperature the mixture was diluted with water (20 ml) and extracted with ethyl acetate (20 ml). The aqueous component was separated and extracted with ethyl acetate (20 ml). The combined organic components were dried (Na₂SO₄), filtered and concentrated to give a brown oil. The crude product mixture was purified by column chromatography (eluding with 100percent DCM-->90:10:1 DCM:MeOH:NH₃) to give the desired product as a white solid (1.0 g, 97percent). ¹H NMR (400 MHz, CDCl₃) δ ppm 2.01-2.20 (m, 3H), 3.41-3.60 (m, 4H), 4.58-4.61 (m, 1H), 6.23 (d, 1H), 7.45 (dd, 1H), 8.11 (d, 1H). LRMS m/z (APCI) 377 [MH⁺].
55%	for 20 h; Heating / reflux	A mixture of 2,5-dibromopyridine (28.6 g, 121 mmol) and (S)-3-hydroxypyrrolidine (10.0 g, 115 mmol) in dry toluene (150 mL) was stirred under reflux for 20 h. The mixture was allowed to cool to rt, and the solvents were removed under reduced pressure. The residue was dissolved with EtOAc, and the resulting mixture was washed with aq. 10percent K₂CO₃. The org. layer was dried over MgSO₄, filtered, and the solvents were concentrated under reduced pressure. Purification of the residue by FC(CH₂Cl₂/MeOH 99:1-->98:2-->97:3-->96:4-->95:5-->94:6-->93:7) yielded the title compound (15.39 g, 55percent). LC-MS: t_R=0.45 min; ES+: 245.11.
46%	Stage #1: Heating / reflux Stage #2: With potassium carbonate In water; ethyl acetate	A mixture of 2,5-dibromopyridine (12.2 g, 51.5 mmol) and (S)-hydroxypyrrolidine (2.80 g, 32.1 mmol) in toluene (50 mL) was heated to reflux overnight. The mixture was allowed to cool to rt, and the solvents were removed under reduced pressure. The residue was dissolved with EtOAc (150 mL), and the mixture was washed with aq. 10percent K₂CO₃. The org. layer was dried over MgSO₄, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane-->heptane/EtOAc 1:2) yielded the title compound (3.62 g, 46percent). LC-MS: t_R=0.48 min; ES+: 243.15.

46%	With potassium carbonate In tolueneHeating / reflux	(S)-1-(5-Bromo-pyridin-2-yl)-pyrrolidin-3-ol (G1) A mixture of 2,5-dibromopyridine (12.2 g, 51.5 mmol) and (S)-hydroxypyrrolidine (2.80 g, 32.1 mmol) in toluene (50 mL) was heated to reflux overnight. The mixture was allowed to cool to rt, and the solvents were removed under reduced pressure. The residue was dissolved with EtOAc (150 mL), and the mixture was washed with aq. 10percent K₂CO₃. The org. layer was dried over MgSO₄, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane-->heptane/EtOAc 1:2) yielded the title compound (3.62 g, 46percent). LC-MS: t_R=0.48 min; ES+: 243.15.
46%	Heating / reflux	(S)-l-(5-Bromo-pyridin-2-yl)-pyrrolidin-3-ol (Gl). A mixture of 2,5-dibromopyridine (12.2 g, 51.5 mmol) and (5)-hydroxypyrrolidine (2.80 g, 32.1 mmol) in toluene (50 mL) was heated to reflux overnight. The mixture was allowed to cool to rt, and the solvents were removed under reduced pressure. The residue was dissolved with EtOAc (150 mL), and the mixture was washed with aq. 10 percent K2CO3. The org. layer was dried over MgSO₄, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane - > heptane/EtOAc 1 :2) yielded the title compound (3.62 g, 46percent). LC-MS: t_R = 0.48 min; ES+: 243.15.

Reference： [1] Patent: US2008/85884, 2008, A1, . Location in patent: Page/Page column 69
[2] Patent: US2009/88457, 2009, A1, . Location in patent: Page/Page column 17
[3] Patent: US2009/62342, 2009, A1, . Location in patent: Page/Page column 11
[4] Patent: US2009/176823, 2009, A1, . Location in patent: Page/Page column 39
[5] Patent: WO2007/88514, 2007, A1, . Location in patent: Page/Page column 104-105
[6] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 21, p. 6291 - 6296

4
[ 766-11-0 ]
[ 100243-39-8 ]
[ 946002-90-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	at 120℃; for 0.75 h; Microwave irradiation	Preparation 53; (S)-l-(5-Bromo-pyridin-2-yl)-pyrrolidin-3-ol; Heat 5-bromo-2-fluoro-pyridine (10.33 g, 57.39 mmmol) in THF (50 mL) with (S)-3-hydroxypyrrolidine (5.00 g, 57.39 mmol) and Et₃N (9.2 mL, 68.87 mmol) in a microwave reactor at 120 ⁰C for 45 min. Dilute with EtOAc (150 mL), and wash with saturated NaHCO₃ (2 x 50 mL) and water (100 mL). Dry with Na₂SO₄, filter, and concentrate. Purify the crude material by chromatography, eluting with 100percent EtOAc to give 10.13 g (72percent) of the title compound. MS/ES m/z (⁷⁹Br) 244.0 [M+H]⁺.

Reference： [1] Patent: WO2007/146759, 2007, A2, . Location in patent: Page/Page column 37

5
[ 100243-39-8 ]
[ 1223405-08-0 ]

Reference： [1] Patent: US2017/281632, 2017, A1, . Location in patent: Paragraph 0382; 0415; 0418

[ 100243-39-8 ] Synthesis Path-Downstream 1~51

1
[ 101385-90-4 ]
[ 100243-39-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrogen;5% palladium over charcoal; In water; at 80℃; for 8h;	A 500 ml four-neck flask equipped with a stirrer, a thermometer, a Dimroth condenser, and a gas introduction pipe was loaded with (S)-1-benzyl-3-hydroxypyrrolidine 52.5 g (0.3 mole, optical purity 99.5%ee), water 210 g, and 5% Pd/C 5.25 g (PE type, 55.27% water content, manufactured by N.E. Chemcat Corp.) and the contents were stirred at 80C for 8 hours under hydrogen ventilation condition. The hydrogen ventilation was stopped and the resulting reaction solution was cooled to a room temperature while being stirred and the catalyst was removed by vacuum filtration. The filtrate was concentrated to about 50 g by an evaporator. The concentrated product was distilled by a distillation apparatus equipped with about 5-step refining distillation towers packed with Heli-pack to obtain (S)-3-hydroxypyrrolidine 23.5 g as a fraction at 1 kPa and tower summit temperature of 93 to 95C. The yield was 90% and the chemical purity was 99.9 area% and an optical purity was 99 . 5 %ee. The water content was 0.3%.

Reference： [1]ARKIVOC,2013,vol. 2014,p. 54 - 64
[2]Tetrahedron,2006,vol. 62,p. 5763 - 5774
[3]Patent: EP1640364,2006,A1 .Location in patent: Page/Page column 12
[4]Journal of Medicinal Chemistry,1994,vol. 37,p. 2138 - 2144
[5]Chemische Berichte,1997,vol. 130,p. 385 - 397

2
[ 501-53-1 ]
[ 100243-39-8 ]
[ 100858-32-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine; In dichloromethane; at 5 - 20℃; for 48h;	Step 1: preparation of benzyl (3S)-3-hydroxypyrrolidine-1-carboxylate. A solution of (3S)-pyrrolidin-3-ol (10.0 g, 0.12 mol) in dichloromethane (130 mL) was cooled to 5C. Triethylamine (16.9 mL, 0.12 mol) was added, followed by drop wise addition ofbenzyl chloroformate (13.9 mL, 0.10 mol), ensuring that the temperature did not exceed5C. The reaction mixture was then allowed to stir at ambient temperature for 48h, after which it was poured into aqueous saturated sodium bicarbonate and extracted into dichloromethane. The combined organic layers were washed with aqueous saturated sodium bicarbonate, dried over magnesium sulfate, and concentrated in vacuo. The resulting crude oil was purified by silica gel column chromatography (50% ether hexanes followed by ether) to afford the title compound as a clear oil (14 g, 92%).

Reference： [1]Patent: WO2014/68527,2014,A1 .Location in patent: Page/Page column 81; 82
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1773 - 1778

3
[ 3398-22-9 ]
[ 100243-39-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1773 - 1778

4
[ 10365-98-7 ]
[ 130115-85-4 ]
[ 100243-39-8 ]
2-chloro-3-(3-methoxy)phenyl-5-(3-(R)-pyrrolidinyloxy)-pyridine [ No CAS ]