(S)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate

Base Information

• Chemical Name: (S)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate
• CAS No.: 1306763-30-3
• Molecular Formula: C₁₅H₁₈N₂O₂
• Molecular Weight: 258.32
• Mol file: 1306763-30-3.mol

Synonyms:(S)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate;Ozanimod intermediate 1

Chemical Property of (S)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate

Chemical Property:

• Boiling Point: 411.9±44.0 °C(Predicted)
• PKA: 11.86±0.20(Predicted)
• PSA: 62.12000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 3.46118
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(R)-tert-Butyl(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (R)-tert-Butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate is a useful reagent in the preparation of oxadiazoles as sphingosine 1 phosphate receptor modulators useful in the treatment of S1P1-associated diseases.

Technology Process of (S)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate

There total 5 articles about (S)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate 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: 84.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-(1-amino-2,3-dihydro-1H-indene-1-yl)-4-carbonitrile hydrochloride (1306763-29-0,1213591-14-0) → (R)-tert-butyl 4-cyano-2,3-dihydro-1H-inden-1-ylcarbamate (1306763-30-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;

Reference yield:

4-bromo-2,3-dihydroinden-1-one (15115-60-3) → (R)-tert-butyl 4-cyano-2,3-dihydro-1H-inden-1-ylcarbamate (1306763-30-3)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1-methyl-pyrrolidin-2-one / 7 h / 95 °C / Inert atmosphere

2: titanium(IV) tetraethanolate / toluene / 12 h / 60 °C / Inert atmosphere

3: sodium tetrahydroborate; tetrahydrofuran / 2.5 h / -78 - 0 °C / Inert atmosphere

4: hydrogenchloride / 1,4-dioxane / 1.5 h / 20 °C

5: triethylamine / dichloromethane / 2 h / 0 - 20 °C

With tetrahydrofuran; hydrogenchloride; titanium(IV) tetraethanolate; sodium tetrahydroborate; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; dichloromethane; toluene;

Reference yield:

4-cyano-2,3-dihydro-1H-inden-1-one (60899-34-5) → (R)-tert-butyl 4-cyano-2,3-dihydro-1H-inden-1-ylcarbamate (1306763-30-3)

Guidance literature:

Multi-step reaction with 4 steps

1: titanium(IV) tetraethanolate / toluene / 12 h / 60 °C / Inert atmosphere

2: sodium tetrahydroborate; tetrahydrofuran / 2.5 h / -78 - 0 °C / Inert atmosphere

3: hydrogenchloride / 1,4-dioxane / 1.5 h / 20 °C

4: triethylamine / dichloromethane / 2 h / 0 - 20 °C

With tetrahydrofuran; hydrogenchloride; titanium(IV) tetraethanolate; sodium tetrahydroborate; triethylamine; In 1,4-dioxane; dichloromethane; toluene;

upstream raw materials:

4-cyano-2,3-dihydro-1H-inden-1-one

di-tert-butyl dicarbonate

(R)-(1-amino-2,3-dihydro-1H-indene-1-yl)-4-carbonitrile hydrochloride

4-bromo-2,3-dihydroinden-1-one

Downstream raw materials:

(R)-tert-butyl 2-(tert-butyldimethylsilyloxy)ethyl(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate

(R)-tert-butyl 4-(5-(3,4-diethoxybenzyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-ylcarbamate

(R)-tert-butyl 2-(tert-butyldimethylsilyloxy)ethyl(4-(N-hydroxycarbamimidoyl)-2,3-dihydro-1H-inden-1-yl)carbamate

(R)-tert-butyl 2-(tert-butyldimethylsilyloxy)ethyl(4-(5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate

Refernces

• 1、 -. "SELECTIVE SPHINGOSINE 1 PHOSPHATE RECEPTOR MODULATORS AND COMBINATION THERAPY THEREWITH". Page/Page column 78-79. . Retrieved 2015/05/19.