(R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(4-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(4-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester
• CAS No.: 218292-39-8
• Molecular Formula: C₂₃H₃₈ClNO₄Si
• Molecular Weight: 456.098
• Mol file: 218292-39-8.mol

Synonyms:(R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(4-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester

Chemical Property of (R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(4-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(4-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester

There total 10 articles about (R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(4-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl 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: 83.0%

[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(4-chloro-phenyl)-2-hydroxy-butyl]-(2-hydroxy-ethyl)-carbamic acid tert-butyl ester → (R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(4-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (218292-39-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; Ambient temperature;

DOI:10.1016/S0957-4166(98)00336-X

Reference yield:

bromochlorobenzene (106-39-8) → (R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(4-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (218292-39-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) Mg, I₂, ZnCl₂, 2.) PdCl₂(PPh₃)2 / 1.) Et₂O, 1 h, 2.) Et₂O, RT, 30 min

2: conc. H₂SO₄ / 0.5 h / Heating

3: 1.) LiAlH₄, 2.) aq. NaOH / 1.) THF, 0 deg C, 30 min, 2.) RT, 1 h

4: Et₃N, 4-dimethylaminopyridine / dimethylformamide / 2 h

5: 95 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O / 8 h / 0 °C

6: pyridine / Ambient temperature

7: LiClO₄ / acetonitrile / 16 h / 100 °C

8: Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

9: 83 percent / PPh₃, diethyl azodicarboxylate / toluene / Ambient temperature

With pyridine; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; lithium aluminium tetrahydride; (DHQD₂)PHPAL); sulfuric acid; iodine; lithium perchlorate; potassium carbonate; magnesium; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; zinc(II) chloride; potassium hexacyanoferrate(III); diethylazodicarboxylate; In dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0957-4166(98)00336-X

Reference yield:

3-(4-chlorophenyl)but-3-en-1-ol (29123-92-0) → (R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(4-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (218292-39-8)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N, 4-dimethylaminopyridine / dimethylformamide / 2 h

2: 95 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O / 8 h / 0 °C

3: pyridine / Ambient temperature

4: LiClO₄ / acetonitrile / 16 h / 100 °C

5: Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

6: 83 percent / PPh₃, diethyl azodicarboxylate / toluene / Ambient temperature

With pyridine; dmap; (DHQD₂)PHPAL); lithium perchlorate; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate; In dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0957-4166(98)00336-X

upstream raw materials:

bromochlorobenzene

3-(4-chlorophenyl)but-3-en-1-ol

3-(4-chlorophenyl)-3-butenoic acid

((3-bromobut-3-en-1-yl)oxy)(tert-butyl)dimethylsilane