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201855-60-9

201855-60-9

Identification

  • Product Name:3-Piperidinemethanol, 4-(4-fluorophenyl)-1-(phenylmethyl)-, (3S,4R)-

  • CAS Number: 201855-60-9

  • EINECS:

  • Molecular Weight:299.388

  • Molecular Formula: C19H22FNO

  • HS Code:

  • Mol File:201855-60-9.mol

Synonyms:[(3S,4R)-1-Benzyl-4-(4-fluorophenyl)piperidin-3-yl]methanol;Paroxetine hydrochloride;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
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  • Manufacture/Brand:TRC
  • Product Description:trans1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol
  • Packaging:250mg
  • Price:$ 165
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Paroxetine hydrochloride (anhydrous) impurity H European Pharmacopoeia (EP) Reference Standard
  • Packaging:y0000581
  • Price:$ 190
  • Delivery:In stock
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:TRANS 1-BENZYL-4-(4-FLUOROPHENYL)-3-PIPERIDINEMETHANOL 95.00%
  • Packaging:2.5G
  • Price:$ 2035
  • Delivery:In stock
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:TRANS 1-BENZYL-4-(4-FLUOROPHENYL)-3-PIPERIDINEMETHANOL 95.00%
  • Packaging:250MG
  • Price:$ 750.75
  • Delivery:In stock
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Relevant articles and documentsAll total 10 Articles be found

Multigram-scale flow synthesis of the chiral key intermediate of (-)-paroxetine enabled by solvent-free heterogeneous organocatalysis

?tv?s, Sándor B.,Pericàs, Miquel A.,Kappe, C. Oliver

, p. 11141 - 11146 (2019/12/28)

The catalytic enantioselective synthesis of the chiral key intermediate of the antidepressant (-)-paroxetine is demonstrated as a continuous flow process on multi-gram scale. The critical step is a solvent-free organocatalytic conjugate addition followed

Catalytic Michael/Ring-Closure Reaction of α,β-Unsaturated Pyrazoleamides with Amidomalonates: Asymmetric Synthesis of (?)-Paroxetine

Zhang, Yu,Liao, Yuting,Liu, Xiaohua,Yao, Qian,Zhou, Yuhang,Lin, Lili,Feng, Xiaoming

, p. 15119 - 15124 (2016/10/11)

A highly enantioselective tandem Michael/ring-closure reaction of α,β-unsaturated pyrazoleamides and amidomalonates has been accomplished in the presence of a chiral N,N′-dioxide–Yb(OTf)3complex (Tf: trifluoromethanesulfonyl) to give various substituted chiral glutarimides with high yields and diastereo- and enantioselectivities. Moreover, this methodology could be used for gram-scale manipulation and was successfully applied to the synthesis of (?)-paroxetine. Further nonlinear and HRMS studies revealed that the real catalytically active species was a monomeric L-PMe2–Yb3+complex. A plausible transition state was proposed to explain the origin of the asymmetric induction.

Optically pure γ-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: A formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide

Devalankar, Dattatray A.,Karabal, Pratibha U.,Sudalai, Arumugam

supporting information, p. 1280 - 1285 (2013/05/08)

The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(iii)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.

Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines

?íhalová, Sylva,Valero, Guillem,Schimer, Ji?í,Humpl, Marek,Dra?ínsky, Martin,Moyano, Albert,Rios, Ramon,Vesely, Jan

scheme or table, p. 8942 - 8950 (2011/12/01)

The synthesis of piperidines and piperidines derivatives in enantiopure fashion has been a challenging goal for organic chemists. In this report we developed a nice cascade reaction for piperidine derivatives based in an amidomalonate Michael addition to enals followed by an intramolecular hemiaminal formation with good yields and enantioselectivities. Moreover we studied the 'in situ' intramolecular cyclization of this hemiaminals with alcohols forming fused piperidine-oxazolidines.

Stereospecific construction of substituted piperidines. Synthesis of (-)-paroxetine and (+)-laccarin

Bower, John F.,Riis-Johannessen, Thomas,Szeto, Peter,Whitehead, Andrew J.,Gallagher, Timothy

, p. 728 - 730 (2007/10/03)

Short and efficient enantioselective syntheses of (-)-paroxetine and (+)-laccarin are described based on the highly stereospecific cleavage of C(3)-substituted 1,3-cyclic sulfamidates. The Royal Society of Chemistry.

Process route upstream and downstream products

Process route

isobutyl (3S,4R)-1-benzyl-4-(4-fluorophenyl)piperidine-3-carboxylate
369593-39-5

isobutyl (3S,4R)-1-benzyl-4-(4-fluorophenyl)piperidine-3-carboxylate

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol
201855-60-9,188869-25-2

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.833333h;
100%
With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 0.833333h;
100%
(3S,4R)-3-tert-butoxycarbonyl-4-(4-fluorophenyl)-N-benzylpiperidine-2,6-dione

(3S,4R)-3-tert-butoxycarbonyl-4-(4-fluorophenyl)-N-benzylpiperidine-2,6-dione

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol
201855-60-9,188869-25-2

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 60 ℃; for 4h; Inert atmosphere;
65%
(3S,4R)-1-benzyl-4-(4-fluorophenyl)-2-oxopiperidine-3-carboxylic acid methyl ester
216690-18-5

(3S,4R)-1-benzyl-4-(4-fluorophenyl)-2-oxopiperidine-3-carboxylic acid methyl ester

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol
201855-60-9,188869-25-2

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In tetrahydrofuran; for 20h; Heating;
With dimethylsulfide borane complex; In 2-methyltetrahydrofuran; at 90 ℃; for 1.66667h; under 7500.75 Torr; chemoselective reaction; Flow reactor;
4.95 g
malonic acid dibenzyl ester
15014-25-2

malonic acid dibenzyl ester

trans-4-fluorocinnamaldehyde
24654-55-5,51791-26-5,213617-57-3

trans-4-fluorocinnamaldehyde

benzylamine
100-46-9

benzylamine

(-)-trans-1-benzyl-3-hydroxymethyl-4-(4-fluorophenyl)piperidine
188869-25-2

(-)-trans-1-benzyl-3-hydroxymethyl-4-(4-fluorophenyl)piperidine

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol
201855-60-9,188869-25-2

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

Conditions
Conditions Yield
malonic acid dibenzyl ester; trans-4-fluorocinnamaldehyde; With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; In ethanol; at 0 ℃; for 96h;
benzylamine; With sodium tris(acetoxy)borohydride; In 1,4-dioxane; at 0 - 20 ℃; for 24h;
With lithium aluminium tetrahydride; In tetrahydrofuran; Title compound not separated from byproducts; Heating;
(3S,4R)-ethyl 1-benzyl-4-(4-fluorophenyl)-6-hydroxy-2-oxopiperidine-3-carboxylate
323203-13-0

(3S,4R)-ethyl 1-benzyl-4-(4-fluorophenyl)-6-hydroxy-2-oxopiperidine-3-carboxylate

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol
201855-60-9,188869-25-2

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

Conditions
Conditions Yield
With borane-THF; In tetrahydrofuran;
86%
isobutyl (3S,7aR)-5-oxo-3-phenyl-6-(phenylseleno)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate

isobutyl (3S,7aR)-5-oxo-3-phenyl-6-(phenylseleno)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol
201855-60-9,188869-25-2

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: H2O2 / CH2Cl2 / 0.5 h / 0 °C
2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C
2.2: copper iodide / tetrahydrofuran / 0.5 h / -25 °C
2.3: 97 percent / tetrahydrofuran / 2 h / -78 °C
3.1: 44 percent / borane*tetrahydrofuran / tetrahydrofuran / 1.5 h / 20 °C
4.1: methanesulfonyl chloride / 1,2-dichloro-ethane / 0.83 h / 0 °C
4.2: 84 percent / Et3N / 1,2-dichloro-ethane / 36 h / Heating
5.1: 71 percent / nBu3SnH; AIBN / toluene / 1.75 h / Heating
6.1: 100 percent / LiAlH4 / tetrahydrofuran / 0.83 h / 20 °C
With lithium aluminium tetrahydride; n-butyllithium; borane-THF; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; methanesulfonyl chloride; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; toluene;
Multi-step reaction with 6 steps
1.1: H2O2 / CH2Cl2 / 0.5 h / 0 °C
2.1: 97 percent / tetrahydrofuran / 2 h / -78 °C
3.1: 44 percent / BH3*THF / tetrahydrofuran / 1.5 h / 0 °C
4.1: MsCl / 1,2-dichloro-ethane / 1 h / 0 - 20 °C
4.2: 84 percent / Et3N / 1,2-dichloro-ethane / 48 h / Heating
5.1: 71 percent / n-Bu3SnH / AIBN / toluene / 2 h / Heating
6.1: 100 percent / LAH / tetrahydrofuran / 0.83 h / 0 - 20 °C
With lithium aluminium tetrahydride; borane-THF; dihydrogen peroxide; tri-n-butyl-tin hydride; methanesulfonyl chloride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene;
isobutyl (3S,6S,7R,7aR)-7-(4-fluorophenyl)-3-phenyl-5-oxo-tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate
369593-36-2

isobutyl (3S,6S,7R,7aR)-7-(4-fluorophenyl)-3-phenyl-5-oxo-tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol
201855-60-9,188869-25-2

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: 44 percent / borane*tetrahydrofuran / tetrahydrofuran / 1.5 h / 20 °C
2.1: methanesulfonyl chloride / 1,2-dichloro-ethane / 0.83 h / 0 °C
2.2: 84 percent / Et3N / 1,2-dichloro-ethane / 36 h / Heating
3.1: 71 percent / nBu3SnH; AIBN / toluene / 1.75 h / Heating
4.1: 100 percent / LiAlH4 / tetrahydrofuran / 0.83 h / 20 °C
With lithium aluminium tetrahydride; borane-THF; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; methanesulfonyl chloride; In tetrahydrofuran; 1,2-dichloro-ethane; toluene;
Multi-step reaction with 4 steps
1.1: 44 percent / BH3*THF / tetrahydrofuran / 1.5 h / 0 °C
2.1: MsCl / 1,2-dichloro-ethane / 1 h / 0 - 20 °C
2.2: 84 percent / Et3N / 1,2-dichloro-ethane / 48 h / Heating
3.1: 71 percent / n-Bu3SnH / AIBN / toluene / 2 h / Heating
4.1: 100 percent / LAH / tetrahydrofuran / 0.83 h / 0 - 20 °C
With lithium aluminium tetrahydride; borane-THF; tri-n-butyl-tin hydride; methanesulfonyl chloride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; 1,2-dichloro-ethane; toluene;
isobutyl (3S,4R,5S)-1-benzyl-4-(4-fluorophenyl)-5-(hydroxymethyl)pyrrolidine-3-carboxylate
369593-37-3

isobutyl (3S,4R,5S)-1-benzyl-4-(4-fluorophenyl)-5-(hydroxymethyl)pyrrolidine-3-carboxylate

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol
201855-60-9,188869-25-2

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: methanesulfonyl chloride / 1,2-dichloro-ethane / 0.83 h / 0 °C
1.2: 84 percent / Et3N / 1,2-dichloro-ethane / 36 h / Heating
2.1: 71 percent / nBu3SnH; AIBN / toluene / 1.75 h / Heating
3.1: 100 percent / LiAlH4 / tetrahydrofuran / 0.83 h / 20 °C
With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; methanesulfonyl chloride; In tetrahydrofuran; 1,2-dichloro-ethane; toluene;
Multi-step reaction with 3 steps
1.1: MsCl / 1,2-dichloro-ethane / 1 h / 0 - 20 °C
1.2: 84 percent / Et3N / 1,2-dichloro-ethane / 48 h / Heating
2.1: 71 percent / n-Bu3SnH / AIBN / toluene / 2 h / Heating
3.1: 100 percent / LAH / tetrahydrofuran / 0.83 h / 0 - 20 °C
With lithium aluminium tetrahydride; tri-n-butyl-tin hydride; methanesulfonyl chloride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; 1,2-dichloro-ethane; toluene;
isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate
369593-38-4

isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol
201855-60-9,188869-25-2

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 71 percent / nBu3SnH; AIBN / toluene / 1.75 h / Heating
2: 100 percent / LiAlH4 / tetrahydrofuran / 0.83 h / 20 °C
With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; toluene;
Multi-step reaction with 2 steps
1: 71 percent / n-Bu3SnH / AIBN / toluene / 2 h / Heating
2: 100 percent / LAH / tetrahydrofuran / 0.83 h / 0 - 20 °C
With lithium aluminium tetrahydride; tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; toluene;
(3S,4R)-1-benzyl-4-(4-fluorophenyl)-2-oxopiperidine-3-carboxylic acid methyl ester
216690-18-5

(3S,4R)-1-benzyl-4-(4-fluorophenyl)-2-oxopiperidine-3-carboxylic acid methyl ester

C<sub>20</sub>H<sub>22</sub>FNO<sub>2</sub>

C20H22FNO2

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol
201855-60-9,188869-25-2

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

Conditions
Conditions Yield
With dimethylsulfide borane complex; In 2-methyltetrahydrofuran; at 90 ℃; under 7500.75 Torr; Temperature; chemoselective reaction; Flow reactor;

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