(S)-1-Boc-3-hydroxypiperidine

Base Information

• Chemical Name: (S)-1-Boc-3-hydroxypiperidine
• CAS No.: 143900-44-1
• Molecular Formula: C10H19NO3
• Molecular Weight: 201.266
• Hs Code.: 29339900
• European Community (EC) Number: 626-373-5
• DSSTox Substance ID: DTXSID20363881
• Nikkaji Number: J1.697.550H
• Wikidata: Q72449629
• Mol file: 143900-44-1.mol

Synonyms:(S)-1-Boc-3-hydroxypiperidine;143900-44-1;(S)-tert-Butyl 3-hydroxypiperidine-1-carboxylate;(S)-N-Boc-3-hydroxypiperidine;(S)-1-N-Boc-3-Hydroxy-piperidine;tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate;(S)-1-N-Boc-3-hydroxypiperidine;Ibrutinib Interm 0441;(S)-1-Boc-3-piperidinol;(S)-3-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester;(S)-N-Boc-3-hydroxy piperidine;((S)-1-Boc-3-hydroxypiperidine);MFCD04115307;1-PIPERIDINECARBOXYLIC ACID, 3-HYDROXY-, 1,1-DIMETHYLETHYL ESTER, (3S)-;(S)-1-(tert-Butoxycarbonyl)-3-hydroxypiperidine;S-1-BOC-3-Hydroxy-piperidine;(S)-1-Boc-3-hydroxylpiperidine;(S)-N-tert-Butoxycarbonyl-3-hydroxypiperidine;(3S)-3-Hydroxypiperidine;tert-butyl (S)-3-hydroxypiperidine-1-carboxylate;(3S)-1-(tert-Butoxycarbonyl)-3-hydroxypiperidine;S-1-Boc-3-hydroxypiperidine;SCHEMBL1068107;(S)-3-hydroxy-N-Boc-piperidine;DTXSID20363881;CS-B0411;AKOS007930567;(S)-3-hydroxypiperidine-1-carboxylate;AC-2186;(S)-1-Boc-3-hydroxypiperidine, 97%;(s)-3-hydroxypiperidine, n-boc protected;AS-37122;AM20080331;B4446;EN300-95051;(3S)-1-(tert-Butyloxycarbonyl)piperidine-3-ol;(s)-3-hydroxy-1-(tert-butoxycarbonyl)piperidine;(S)-tert-butyl3-hydroxypiperidine-1-carboxylate;(3S)-3-HYDROXYPIPERIDINE, N-BOC PROTECTED;(s)-tert butyl-3-hydroxypiperidine-1-carboxylate;tert-butyl (3S)-3-hydroxypiperidine-l-carboxylate;tert-butyl(3S)-3-hydroxypiperidine-1-carboxylate;tert-butyl-(3S)-3-hydroxypiperidine-1-carboxylate;(3S)-3-hydroxy piperidine-1-carboxylate tert-butyl;Q-200033;(S)-3-hydroxypiperidine-1-carboxylic acid tert-butyl ester;1,1-dimethylethyl (3S)-3-hydroxypiperidine-1-carboxylate;(S)-tert-Butyl-3-hydroxypiperidine-1-carboxylate tert- butyl;(3S)-hydroxy-1-piperidinecarboxylic acid 1,1-dimethylethyl ester

Chemical Property of (S)-1-Boc-3-hydroxypiperidine

Chemical Property:

• Vapor Pressure: 0.000198mmHg at 25°C
• Melting Point: 34-40 °C
• Refractive Index: 1.495
• Boiling Point: 292.3 °C at 760 mmHg
• PKA: 14.74±0.20(Predicted)
• Flash Point: 130.6 °C
• PSA: 49.77000
• Density: 1.107 g/cm³
• LogP: 1.31610
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Soluble in methanol.
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 201.13649347
• Heavy Atom Count: 14
• Complexity: 210

Purity/Quality:

≥98.0% ^*data from raw suppliers

(S)-1-Boc-3-hydroxypiperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC(C1)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCC[C@@H](C1)O
• Uses: (S)-1-Boc-3-hydroxypiperidine is an important chiral intermediate for the synthesis of ibrutinib, an anticancer drug targeting B-cell malignancies. Synthesis of pharmaceutical intermediates including ibrutinib, the API of the newly approved drug Imbruvica, for the treatment of lymphoma. A piperidine derivative with an amine protecting group, (S)-1-Boc-3-hydroxypiperidine can be used in the preparation of biologically active compounds such as antagonists of the human P2X7 receptor and selective irreversible inhibitors for bruton's tyrosine kinase. (S)-1-Boc-3-hydroxypiperidine is used as pharmaceutical intermediate.

Technology Process of (S)-1-Boc-3-hydroxypiperidine

There total 53 articles about (S)-1-Boc-3-hydroxypiperidine 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: 98.9%

(S)-3-hydroxypiperidine hydrochloride (475058-41-4,198976-43-1) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate (143900-44-1)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 66h;

Reference yield: 98.08%

3-oxo-piperidine-1-carboxylic acid tert-butyl ester (98977-36-7) → tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate (143900-44-1)

Guidance literature:

With rac-octan-2-ol; In aq. buffer; at 35 ℃; for 12h; pH=8; Reagent/catalyst; pH-value; Temperature; enantioselective reaction; Enzymatic reaction;

DOI:10.3390/molecules23123117

Reference yield: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-3-hydroxypiperidine D-pyroglutamate → tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate (143900-44-1)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 3h; Time; Large scale;

upstream raw materials:

vinyl acetate

N-tert-butoxycarbonyl-3-piperidinol

di-tert-butyl dicarbonate

(S)-3-hydroxypiperidine hydrochloride

Downstream raw materials:

tert-butyl (+)-(3S)-3-(benzyloxy)piperidine carbamate

tert-butyl (R)-3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylate

(R)-5-(4-phenoxyphenyl)-7-(piperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

tert-butyl (R)-3-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylate

Refernces

• 1、 Ying, Xiangxian,Zhang, Jie,Wang, Can,Huang, Meijuan,Ji, Yuting,Cheng, Feng,Yu, Meilan,Wang, Zhao,Ying, Meirong. "Characterization of a carbonyl reductase from Rhodococcus erythropolis WZ010 and its variant Y54F for asymmetric synthesis of (S)-N-Boc-3-hydroxypiperidine". . . Retrieved 2018.
• 2、 Wu, Yanfei,Zhou, Jieyu,Ni, Jie,Zhu, Cheng,Sun, Zewen,Xu, Guochao,Ni, Ye. "Engineering an Alcohol Dehydrogenase from Kluyveromyces polyspora for Efficient Synthesis of Ibrutinib Intermediate". . . Retrieved 2021/02/26.
• 3、 -. "Preparation method of (S)-1-tert-butyloxycarbonyl-3-hydroxypiperidine". . . Retrieved 2020/03/25.