1H-Indole-1-carboxylic acid, 5-(hydroxymethyl)-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: 1H-Indole-1-carboxylic acid, 5-(hydroxymethyl)-, 1,1-dimethylethyl ester
• CAS No.: 279255-90-2
• Molecular Formula: C14H17NO3
• Molecular Weight: 247.29000
• Hs Code.: 2933990090
• Mol file: 279255-90-2.mol

Synonyms:(N-tert-butoxycarbonyl)indole-5-methanol;5-hydroxymethylindole-1-carbamic acid tert-butyl ester;1-(t-butyloxycarbonyl)-5-hydroxymethylindole;N-tert-butoxycarbonylindol-5-yl methanol;1-Boc-5-hydroxymethylindole;1-Boc-5-(hydroxymethyl)-1H-Indole;5-HYDROXYMETHYL-INDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;

Chemical Property of 1H-Indole-1-carboxylic acid, 5-(hydroxymethyl)-, 1,1-dimethylethyl ester

Chemical Property:

• Boiling Point: 396.0±34.0 °C(Predicted)
• PKA: 14.37±0.10(Predicted)
• PSA: 51.46000
• Density: 1.14±0.1 g/cm3(Predicted)
• LogP: 2.91680
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

1-Boc-1H-indol-5-ylmethanol 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Indole-1-carboxylic acid, 5-(hydroxymethyl)-, 1,1-dimethylethyl ester

There total 8 articles about 1H-Indole-1-carboxylic acid, 5-(hydroxymethyl)-, 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: 94.0%

1-(tert-butyloxycarbonyl)indole-5-carboxaldehyde (279256-09-6) → tert-butyl 5-(hydroxymethyl)-1H-indole-1-carboxylate (279255-90-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 1h; Inert atmosphere; Cooling with ice;

DOI:10.1021/jacs.7b03371

Reference yield: 68.0%

5-(carboxymethyl)-indole-1-carbamic acid tert-butyl ester → tert-butyl 5-(hydroxymethyl)-1H-indole-1-carboxylate (279255-90-2)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 2.5h;

Reference yield: 11.0%

(R)-2-amino-4-methylpentanamide (15893-47-7) + 1-(tert-butyloxycarbonyl)indole-5-carboxaldehyde (279256-09-6) → tert-butyl 5-(hydroxymethyl)-1H-indole-1-carboxylate (279255-90-2) + 2R-(1-t-butyloxycarbonylindol-5-ylmethylamino)-4-methyl-pentanamide (879887-21-5) + 2R-bis-(1-t-butyloxycarbonylindol-5-ylmethyl)amino-4-methylpentanamide (879887-65-7)

Guidance literature:

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 8h;

upstream raw materials:

(R)-2-amino-4-methylpentanamide

1-(tert-butyloxycarbonyl)indole-5-carboxaldehyde

1-tert-butoxycarbonyl-5-methoxycarbonylindole

5-(tert-Butyl-dimethyl-silanyloxymethyl)-indole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

2(R)-[(N-tert-butoxy-carbonylindol-5-ylmethyl)-(4-methoxybenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester

1-(tert-butyloxycarbonyl)indole-5-carboxaldehyde

t-butyl 5-(bromomethyl)-1H-indole-1-carboxylate

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