(S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-1-phenyl-ethanol

Base Information

• Chemical Name: (S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-1-phenyl-ethanol
• CAS No.: 250596-58-8
• Molecular Formula: C₂₂H₃₃NO₂Si
• Molecular Weight: 371.595
• Mol file: 250596-58-8.mol

Synonyms:(S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-1-phenyl-ethanol

Chemical Property of (S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-1-phenyl-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-1-phenyl-ethanol

There total 1 articles about (S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-1-phenyl-ethanol 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: 78.0%

(S)-styrene oxide (20780-54-5) + (1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethanamine (120417-13-2,120666-55-9) → (S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-1-phenyl-ethanol (250596-58-8)

Guidance literature:

In methanol; at 40 ℃; for 10h;

DOI:10.1016/S0040-4039(99)01530-0

Reference yield: 76.0%

chloroacetyl chloride (79-04-9) + (S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-1-phenyl-ethanol (250596-58-8) → N-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-2-chloro-N-(2-hydroxy-2-phenyl-ethyl)-acetamide (250596-62-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 2h;

DOI:10.1016/S0040-4039(99)01530-0

Reference yield:

(S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-1-phenyl-ethanol (250596-58-8) → (2R,6S)-4-((R)-2-Hydroxy-1-phenyl-ethyl)-2-methyl-6-phenyl-morpholin-3-one

Guidance literature:

Multi-step reaction with 4 steps

1.1: 76 percent / aq. NaOH / tetrahydrofuran / 2 h

2.1: 90 percent / NaH / tetrahydrofuran / 10 h

3.1: 86 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

4.1: sec-BuLi; HMPA / tetrahydrofuran / 0.5 h / -78 °C

4.2: 74 percent / tetrahydrofuran / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; tetrabutyl ammonium fluoride; sec.-butyllithium; sodium hydride; In tetrahydrofuran; 1.1: Acylation / 2.1: Cyclization / 3.1: desilylation / 4.1: Metallation / 4.2: Methylation;

DOI:10.1016/S0040-4039(99)01530-0

upstream raw materials:

(S)-styrene oxide

(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethanamine

Downstream raw materials:

N-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-2-chloro-N-(2-hydroxy-2-phenyl-ethyl)-acetamide

(S)-4-((R)-2-Hydroxy-1-phenyl-ethyl)-6-phenyl-morpholin-3-one