250589-64-1

Basic information

• Product Name: (2S,3S)-1-N-BENZYL-3-HYDROXY-2-PHENYLPIPERIDINE
• Synonyms: 3-Piperidinol, 2-phenyl-1-(phenylmethyl)-, (2S,3S)-
• CAS NO: 250589-64-1
• Molecular Formula: C18H21NO
• Molecular Weight: 267.37
• Mol File: 250589-64-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 400.4°C at 760 mmHg
• Flash Point: 103.1°C
• Appearance: /
• Density: 1.128g/cm³
• Vapor Pressure: 3.95E-07mmHg at 25°C
• Refractive Index: 1.606
• CAS DataBase Reference: (2S,3S)-1-N-BENZYL-3-HYDROXY-2-PHENYLPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-1-N-BENZYL-3-HYDROXY-2-PHENYLPIPERIDINE(250589-64-1)
• EPA Substance Registry System: (2S,3S)-1-N-BENZYL-3-HYDROXY-2-PHENYLPIPERIDINE(250589-64-1)

Safety Data

• Hazardous Substances Data: 250589-64-1(Hazardous Substances Data)

Usage

General Description

(2S,3S)-1-N-benzyl-3-hydroxy-2-phenylpiperidine is a chemical compound with a piperidine backbone and a benzyl and hydroxy functional group attached to different carbon atoms. (2S,3S)-1-N-BENZYL-3-HYDROXY-2-PHENYLPIPERIDINE is a chiral molecule with two stereocenters, and it exists as a pair of enantiomers. Piperidine derivatives like (2S,3S)-1-N-benzyl-3-hydroxy-2-phenylpiperidine have been investigated for their potential applications in pharmaceuticals and biological research, as they can exhibit various pharmacological activities. The hydroxy and benzyl groups can also impart specific chemical reactivity and solubility to the compound, making it suitable for use in various chemical reactions and formulations.

InChI:InChI=1/C18H21NO/c20-17-12-7-13-19(14-15-8-3-1-4-9-15)18(17)16-10-5-2-6-11-16/h1-6,8-11,17-18,20H,7,12-14H2/t17-,18-/m0/s1

Upstream product

• 220058-27-5 trans (2S,3R)-N-benzyl-3-acetoxy-2-phenylpiperidine 
• 271588-24-0 (2S)-1-benzyl-2-phenylpiperidin-3-one 
• 374094-73-2 (1R,2R)-(1-benzylpyrrolidin-2-yl)phenylmethanol 
• 55456-48-9 ((2S)-1-p-toluenesulfonyl-2-pyrrolidinyl)methanol 
• 100-58-3 phenylmagnesium bromide 
• 147-85-3 L-proline 
• 100-39-0 benzyl bromide 
• 74936-95-1 (S)-α-<(R)-pyrrolidin-2-yl>benzyl alcohol 
• 220058-21-9 (R)-1-[(2S)-1-benzylpyrrolidin-2-yl](phenyl)methanol 
• 67488-65-7 (S)-methyl 1-tosylpyrrolidine-2-carboxylate 
• 101250-69-5 (S)-1-<(4-methylphenyl)sulfonyl>-2-pyrrolidinecarboxaldehyde 
• 110529-27-6 (S)-1-[(2S)-1-benzylpyrrolidin-2-yl](phenyl)methanol 
• 1147426-75-2 (1S,2R)-(1-benzylpyrrolidin-2-yl)phenylmethanol 
• 121440-87-7 (+)-(S,E)-N-benzyl-(1,3-diphenyl-2-propenyl)amine 

Downstream Products

• 159249-47-5 tert-butyl (2S,3S)-3-hydroxy-2-phenylpiperidine-1-carboxylate 
• 250589-63-0 (2S,3R)-tert-butyl 3-hydroxy-2-phenylpiperidine-1-carboxylic acid 
• 148687-76-7 (2S,3S)-3-[[3,5-bis(trifluoromethyl)phenyl]methoxy]-2-phenylpiperidine hydrochloride 

Relevant articles and documents

Highly stereoselective syntheses of proline-derived vicinal amino alcohols through grignard addition onto N-tosylprolinal

A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.

Concise, stereodivergent and highly stereoselective synthesis of cis-and trans-2-substituted 3-hydroxypiperidines-development of a phosphite-driven cyclodehydration

A concise (5 to 6 steps), stereodivergent, highly diastereoselective (dr up to >19:1 for both stereoisomers) and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, a core motif in numerous bioactive compounds, is presented. This sequence allowed an efficient synthesis of the NK-1 inhibitor L-733,060 in 8 steps. Additionally, a cyclodehydration-realizing simple triethylphosphite as a substitute for triphenylphosphine is developed. Here the stoichiometric oxidized P(V)-byproduct (triethylphosphate) is easily removed during the work up through saponification overcoming separation difficulties usually associated to triphenylphosphine oxide.

Enantioselective ring expansion of prolinols: An efficient and short synthesis of 2-phenylpiperidin-3-ol derivatives and 3-hydroxypipecolic acids

A very short route to 2-phenylpiperidin-3-ol derivatives and 3-hydroxypipecolic acids is described. The approach uses two key steps: a one-pot reduction/Grignard addition sequence applied to alkyl proline esters and a ring expansion applied to the corresp