1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl ester, (3R)-

Base Information

• Chemical Name: 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl ester, (3R)-
• CAS No.: 942142-74-7
• Molecular Formula: C17H24ClNO3
• Molecular Weight: 325.835
• Mol file: 942142-74-7.mol

Synonyms:(R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate;tert-butyl (R)-3-(3-chlorobenzoyl)piperidine-1-carboxylate;(3-chlorophenyl)((R)-N-Boc-piperidin-3-yl)methanone;(R)-tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate;3-[(3-chlorophenyl)-oxomethyl]-1-piperidinecarboxylic acid tert-butyl ester;1-PIPERIDINECARBOXYLIC ACID, 3-[(R)-(3-CHLOROPHENYL)HYDROXYMETHYL]-, 1,1-DIMETHYLETHYL ESTER, (3R)-;tert-butyl 3-(3-chlorophenyl)carbonylpiperidine-1-carboxylate;tert-butyl (3R)-3-[(R)-(3-chlorophenyl)(hydroxy)-methyl]-1-piperidinecarboxylate;tert-butyl (R)-3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate;tert-Butyl (3R)-3-[(3-chlorophenyl)carbonyl]-1-piperidinecarboxylate;

Chemical Property of 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl ester, (3R)-

Chemical Property:

• Vapor Pressure: 2.99E-08mmHg at 25°C
• Boiling Point: 432.6°C at 760 mmHg
• Flash Point: 215.4°C
• PSA: 49.77000
• Density: 1.192g/cm³
• LogP: 3.95840

Purity/Quality:

NLT 98% ^*data from raw suppliers

1-Piperidinecarboxylicacid,3-[(R)-(3-chlorophenyl)hydroxymethyl]-,1,1-dimethylethylester,(3R)- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl ester, (3R)-

There total 4 articles about 1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl ester, (3R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

(R)-tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate (884512-09-8,1438393-11-3) → (R)-tert-butyl 3-((S)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate + (R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate (942142-74-7)

Guidance literature:

With hydrogen; sodium hydroxide; (S)-2-[(Sp)-2-(diphenylphosphino)ferrocenyl]-4-isopropyl-2-oxazoline triphenylphosphine ruthenium(II) chloride complex; In tert-butyl methyl ether; water; at 20 ℃; for 22h; under 3000.3 Torr;

Reference yield: 43.0%

(R)-tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate (884512-09-8,1438393-11-3) → (R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate (942142-74-7)

Guidance literature:

With (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In toluene; at -14 ℃; for 16h; stereoselective reaction;

DOI:10.1016/j.bmcl.2009.11.066

Reference yield:

(R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (884510-86-5) → (R)-tert-butyl 3-((S)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate + (R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate (942142-74-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: R-CBS-oxazaborolidine / tetrahydrofuran; toluene / -15 °C / Inert atmosphere

2.2: -15 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane; toluene;

DOI:10.1021/ml200137x

upstream raw materials:

(R)-tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate

(R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

(R)-1-Boc-nipecotic acid

Downstream raw materials:

(R)-tert-butyl 3-((R)-(2-(tert-butyldimethylsilyloxy)ethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(3-cyanopropoxy)methyl)piperidine-1-carboxylate

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2,2-dimethoxypropoxy)methyl)piperidine-1-carboxylate

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-ethoxy-2-oxoethoxy)methyl)piperidine-1-carboxylate