(1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide

Base Information

• Chemical Name: (1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide
• CAS No.: 208344-72-3
• Molecular Formula: C₂₂H₂₇NO₃
• Molecular Weight: 353.461
• Mol file: 208344-72-3.mol

Synonyms:(1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide

Chemical Property of (1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide

There total 2 articles about (1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide 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:

3-methyl-2-buten-1-yl diazoacetate (72800-60-3) → (1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide (208344-72-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Rh₂<5(S)-MEPY>4 / CH₂Cl₂ / Heating

2: 1.) Me₃Al / 1.) hexane, 1,2-dichloroethane, RT, 30 min, 2.) hexane, 1,2-dichloroethane, reflux, 24 h

With trimethylaluminum; Doyle dirhodium catalyst; In dichloromethane;

DOI:10.1021/jm980033d

Reference yield:

benzyl-(4-methoxybenzyl)amine (14429-02-8) + (1S,5R)-(-)-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one (82442-72-6) → (1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide (208344-72-3)

Guidance literature:

With trimethylaluminum; Yield given. Multistep reaction; 1.) hexane, 1,2-dichloroethane, RT, 30 min, 2.) hexane, 1,2-dichloroethane, reflux, 24 h;

DOI:10.1021/jm980033d

Reference yield: 93.0%

(1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide (208344-72-3) → (1S,3R)-3-Formyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide (208344-74-5)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1021/jm980033d

upstream raw materials:

benzyl-(4-methoxybenzyl)amine

(1S,5R)-(-)-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one

3-methyl-2-buten-1-yl diazoacetate

Downstream raw materials:

(1S,3R)-3-Formyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide

(1S,3S)-3-Benzylcarbamoyl-2,2-dimethyl-cyclopropanecarboxylic acid

(1S,3S)-3-[Benzyl-(4-methoxy-benzyl)-carbamoyl]-2,2-dimethyl-cyclopropanecarboxylic acid

(1S,3S)-3-Formyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide