tert-butyl [(4R)-2,2-dimethyl-4-(iodomethyl)-1,3-oxazolidin-3-yl]carboxylate

Base Information

• Chemical Name: tert-butyl [(4R)-2,2-dimethyl-4-(iodomethyl)-1,3-oxazolidin-3-yl]carboxylate
• CAS No.: 1231672-20-0
• Molecular Formula: C₁₁H₂₀INO₃
• Molecular Weight: 341.189
• Mol file: 1231672-20-0.mol

Synonyms:tert-butyl [(4R)-2,2-dimethyl-4-(iodomethyl)-1,3-oxazolidin-3-yl]carboxylate

Chemical Property of tert-butyl [(4R)-2,2-dimethyl-4-(iodomethyl)-1,3-oxazolidin-3-yl]carboxylate

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

(R)-N-Boc-4-(iodomethyl)-2,2-dimethyloxazolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl [(4R)-2,2-dimethyl-4-(iodomethyl)-1,3-oxazolidin-3-yl]carboxylate

There total 5 articles about tert-butyl [(4R)-2,2-dimethyl-4-(iodomethyl)-1,3-oxazolidin-3-yl]carboxylate 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: 74.0%

tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (108149-63-9,108149-65-1) → tert-butyl [(4R)-2,2-dimethyl-4-(iodomethyl)-1,3-oxazolidin-3-yl]carboxylate (1231672-20-0)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 20 ℃; for 24h;

DOI:10.3998/ark.5550190.0011.910

Reference yield:

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester (136703-59-8) → tert-butyl [(4R)-2,2-dimethyl-4-(iodomethyl)-1,3-oxazolidin-3-yl]carboxylate (1231672-20-0)

Guidance literature:

Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate / acetone

2: diisobutylaluminium hydride / toluene / -78 °C

3: 1H-imidazole; iodine; triphenylphosphine / toluene / 5 h / 20 °C

With 1H-imidazole; boron trifluoride diethyl etherate; iodine; diisobutylaluminium hydride; triphenylphosphine; In acetone; toluene;

DOI:10.1039/c4md00136b

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl [(4R)-2,2-dimethyl-4-(iodomethyl)-1,3-oxazolidin-3-yl]carboxylate (1231672-20-0)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydroxide / tert-butyl alcohol; water

2: potassium carbonate / N,N-dimethyl-formamide

3: boron trifluoride diethyl etherate / acetone

4: diisobutylaluminium hydride / toluene / -78 °C

5: 1H-imidazole; iodine; triphenylphosphine / toluene / 5 h / 20 °C

With 1H-imidazole; boron trifluoride diethyl etherate; iodine; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; sodium hydroxide; In water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

DOI:10.1039/c4md00136b

upstream raw materials:

tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

di-tert-butyl dicarbonate

3-tert-butoxycarbonylamino-4-hydroxy-butyric acid

Downstream raw materials:

Boc-(S)-2-(3,4-dimethoxyphenethyl)-1,2,3,4-tetrahydroquinoline

Refernces

• 1、 Ollivier, Anthony,Goubert, Marlene,Tursun, Ahmatjan,Canet, Isabelle,Sinibaldia, Marie-Eve. "Orthogonally protected glycerols and 2-aminodiols: Useful building blocks in heterocyclic chemistry". experimental part. p. 108 - 126. Retrieved 2010/10/03.