(1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide

Base Information

• Chemical Name: (1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide
• CAS No.: 253665-35-9
• Molecular Formula: C₂₀H₃₁NO₂SSi
• Molecular Weight: 377.623
• Mol file: 253665-35-9.mol

Synonyms:(1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide

Chemical Property of (1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide

There total 2 articles about (1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide 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: 70.0%

benzaldehyde (100-52-7) + (1S,2R,4R,SS)-7,7-dimethyl-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide (253665-34-8) → (1S,2R,4R,SS)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide (253665-35-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -20 - 20 ℃;

DOI:10.1021/jo990913f

Reference yield:

(1S,5R,7R,SS)-10,10-dimethyl-4-oxo-3-thiatricyclo[5.2.1.01,5]decane-3-oxide (178455-82-8) → (1S,2R,4R,SS)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide (253665-35-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiHMDS / tetrahydrofuran / 3 h / -30 °C

1.2: 40 percent / tetrahydrofuran / 2 h / -30 °C

2.1: 70 percent / n-BuLi / tetrahydrofuran; hexane / -20 - 20 °C

With n-butyllithium; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; 1.1: Ring cleavage / 1.2: Substitution / 2.1: Condensation;

DOI:10.1021/jo990913f

Reference yield:

1-phenoxy-1-trimethylsilyloxyethene (111061-31-5) + (1S,2R,4R,SS)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide (253665-35-9) → methyl (S)-3-amino-3-phenyl-2,2-dimethylpropionate + (R)-methyl 3-amino-2,2-dimethyl-3-phenylpropionate

Guidance literature:

1-phenoxy-1-trimethylsilyloxyethene; (1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -70 ℃; for 6h;

With water; In dichloromethane; at 20 ℃; for 0.5h;

With water; sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jo990913f

upstream raw materials:

benzaldehyde

(1S,2R,4R,S_S)-7,7-dimethyl-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide

(1S,5R,7R,S_S)-10,10-dimethyl-4-oxo-3-thiatricyclo[5.2.1.0^1,5]decane-3-oxide

Downstream raw materials:

ethyl (3S)-3-amino-3-phenylpropionate

(R)-3-amino-3-phenylpropionic acid ethyl ester

4-ethoxy-6-phenyl-5,6-dihydro-1H-pyridin-2-one

(R)-(+)-6-phenylpiperidine-2,4-dione

Refernces