(1S,2R)-cis-2-(tert-butyldiphenylsilyloxymethyl)-N-methoxy-N-methyl-1-cyclopropanecarboxamide

Base Information

• Chemical Name: (1S,2R)-cis-2-(tert-butyldiphenylsilyloxymethyl)-N-methoxy-N-methyl-1-cyclopropanecarboxamide
• CAS No.: 910630-47-6
• Molecular Formula: C₂₃H₃₁NO₃Si
• Molecular Weight: 397.59
• Mol file: 910630-47-6.mol

Synonyms:(1S,2R)-cis-2-(tert-butyldiphenylsilyloxymethyl)-N-methoxy-N-methyl-1-cyclopropanecarboxamide

Chemical Property of (1S,2R)-cis-2-(tert-butyldiphenylsilyloxymethyl)-N-methoxy-N-methyl-1-cyclopropanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-cis-2-(tert-butyldiphenylsilyloxymethyl)-N-methoxy-N-methyl-1-cyclopropanecarboxamide

There total 2 articles about (1S,2R)-cis-2-(tert-butyldiphenylsilyloxymethyl)-N-methoxy-N-methyl-1-cyclopropanecarboxamide 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:

(1S,5R)-3-oxabicyclo[3.1.0]hexan-2-one (75658-86-5) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + tert-butylchlorodiphenylsilane (58479-61-1) → (1S,2R)-cis-2-(tert-butyldiphenylsilyloxymethyl)-N-methoxy-N-methyl-1-cyclopropanecarboxamide (910630-47-6)

Guidance literature:

N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In tetrahydrofuran; hexane; at 20 ℃; for 0.5h;

(1S,5R)-3-oxabicyclo[3.1.0]hexan-2-one; In tetrahydrofuran; hexane; dichloromethane; at 20 ℃; for 5h;

tert-butylchlorodiphenylsilane; With 1H-imidazole; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 30h;

DOI:10.1021/jm0603318

Reference yield:

(1R,5S)-1-(phenylsulfonyl)-3-oxabicyclo[3.1.0]hexan-2-one (408348-28-7) → (1S,2R)-cis-2-(tert-butyldiphenylsilyloxymethyl)-N-methoxy-N-methyl-1-cyclopropanecarboxamide (910630-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Mg; HgCl₂; EtOH / tetrahydrofuran / 5 h / 20 °C

2.1: AlMe₃ / tetrahydrofuran; hexane / 0.5 h / 20 °C

2.2: CH₂Cl₂; tetrahydrofuran; hexane / 5 h / 20 °C

2.3: 395 mg / imidazole / dimethylformamide; CH₂Cl₂; tetrahydrofuran / 30 h / 20 °C

With ethanol; trimethylaluminum; magnesium; mercury dichloride; In tetrahydrofuran; hexane;

DOI:10.1021/jm0603318

Reference yield: 98.0%

(1S,2R)-cis-2-(tert-butyldiphenylsilyloxymethyl)-N-methoxy-N-methyl-1-cyclopropanecarboxamide (910630-47-6) → (1S,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane (408348-34-5)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1h;

DOI:10.1021/jm0603318

upstream raw materials:

(1S,5R)-3-oxabicyclo[3.1.0]hexan-2-one

N,O-dimethylhydroxylamine*hydrochloride

tert-butylchlorodiphenylsilane

(1R,5S)-1-(phenylsulfonyl)-3-oxabicyclo[3.1.0]hexan-2-one

Downstream raw materials:

(1S,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane