Spiro[1H-indene-1,4'-piperidine]-1'-carboxylic acid, 2,3-dihydro-2-hydroxy-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Spiro[1H-indene-1,4'-piperidine]-1'-carboxylic acid, 2,3-dihydro-2-hydroxy-, 1,1-dimethylethyl ester
• CAS No.: 189149-23-3
• Molecular Formula: C18H25NO3
• Mol file: 189149-23-3.mol

Synonyms:

Chemical Property of Spiro[1H-indene-1,4'-piperidine]-1'-carboxylic acid, 2,3-dihydro-2-hydroxy-, 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Spiro[1H-indene-1,4'-piperidine]-1'-carboxylic acid, 2,3-dihydro-2-hydroxy-, 1,1-dimethylethyl ester

There total 4 articles about Spiro[1H-indene-1,4'-piperidine]-1'-carboxylic acid, 2,3-dihydro-2-hydroxy-, 1,1-dimethylethyl ester 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:

1'-(tert-butyloxycarbonyl)spiro<1H-indene-1,4'-piperidine> (137419-24-0) → tert-butyl 3-hydroxy-2,3-dihydrospiro[indene-1,4’-piperidine]-1‘-carboxylate (185525-42-2) + tert-butyl 2-hydroxy-2,3-dihydrospiro[indene-1,4’-piperidine]-1‘-carboxylate (189149-23-3)

Guidance literature:

With sodium hydroxide; borane; dihydrogen peroxide; In tetrahydrofuran;

DOI:10.1016/S0960-894X(97)00075-9

Reference yield:

dimethylsulfide borane complex (13292-87-0) + 1'-(tert-butyloxycarbonyl)spiro<1H-indene-1,4'-piperidine> (137419-24-0) → tert-butyl 3-hydroxy-2,3-dihydrospiro[indene-1,4’-piperidine]-1‘-carboxylate (185525-42-2) + tert-butyl 2-hydroxy-2,3-dihydrospiro[indene-1,4’-piperidine]-1‘-carboxylate (189149-23-3)

Guidance literature:

dimethylsulfide borane complex; 1'-(tert-butyloxycarbonyl)spiro<1H-indene-1,4'-piperidine>; In tetrahydrofuran; at 0 ℃; for 3h;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 1h;

Reference yield:

N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine (118753-70-1) → tert-butyl 3-hydroxy-2,3-dihydrospiro[indene-1,4’-piperidine]-1‘-carboxylate (185525-42-2) + tert-butyl 2-hydroxy-2,3-dihydrospiro[indene-1,4’-piperidine]-1‘-carboxylate (189149-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -50 °C

1.2: 1 h / -50 °C

2.1: tetrahydrofuran / 3 h / 0 °C

2.2: 1 h / 0 °C

With lithium hexamethyldisilazane; In tetrahydrofuran;

upstream raw materials:

1'-(tert-butyloxycarbonyl)spiro<1H-indene-1,4'-piperidine>

N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine

1-indene

dimethylsulfide borane complex

Downstream raw materials:

tert-butyl 2-oxo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

Refernces

• 1、 -. "Novel heterocyclic derivative capable of being used as SHP2 inhibitor". Paragraph 0396; 0398; 0400. . Retrieved 2019/08/30.