Carbamic acid, [1-cyano-2-(hydroxymethyl)cyclopropyl]-, 1,1-dimethylethyl

Base Information

• Chemical Name: Carbamic acid, [1-cyano-2-(hydroxymethyl)cyclopropyl]-, 1,1-dimethylethyl
• CAS No.: 143169-48-6
• Molecular Formula: C₁₀H₁₆N₂O₃
• Molecular Weight: 212.249
• Mol file: 143169-48-6.mol

Synonyms:Carbamic acid, [1-cyano-2-(hydroxymethyl)cyclopropyl]-, 1,1-dimethylethyl

Chemical Property of Carbamic acid, [1-cyano-2-(hydroxymethyl)cyclopropyl]-, 1,1-dimethylethyl

Chemical Property:

• PSA: 82.35000
• LogP: 1.17658

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid, [1-cyano-2-(hydroxymethyl)cyclopropyl]-, 1,1-dimethylethyl

There total 12 articles about Carbamic acid, [1-cyano-2-(hydroxymethyl)cyclopropyl]-, 1,1-dimethylethyl 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:

(1R,2R)-(-)-1--2-<(hexanoyloxy)methyl>cyclopropane-1-carbonitrile (143122-79-6) → (1R,2R)-(+)-1--2-(hydroxymethyl)cyclopropane-1-carbonitrile (143122-80-9) + (1S,2S)-(-)-1--2-(hydroxymethyl)cyclopropane-1-carbonitrile (143169-48-6)

Guidance literature:

at 25 ℃; for 35h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Candida cylindracea, phosphate buffer pH 7.5;

DOI:10.1021/jo00048a028

Reference yield:

(1S,5S)-1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo<3.1.0>hexane (143169-41-9) → (1S,2S)-(-)-1--2-(hydroxymethyl)cyclopropane-1-carbonitrile (143169-48-6)

Guidance literature:

Multi-step reaction with 6 steps

1: TFA / CH₂Cl₂ / 1.33 h / 25 °C

2: NEt₃, (PhO)2PON₃ / 17 h / Heating

3: NH₄OH / 5 h / 25 °C

4: NEt₃, DMAP / CH₂Cl₂ / 1) 0 deg C, 15 min, 2) 25 deg C, 3 h

5: TsCl, pyridine / 12 h / Heating

6: 35 h / 25 °C / Candida cylindracea, phosphate buffer pH 7.5

With pyridine; dmap; ammonium hydroxide; diphenyl phosphoryl azide; triethylamine; p-toluenesulfonyl chloride; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00048a028

Reference yield:

(1R,5S)-2-Oxo-3-oxa-bicyclo[3.1.0]hexane-1-carboxylic acid → (1S,2S)-(-)-1--2-(hydroxymethyl)cyclopropane-1-carbonitrile (143169-48-6)

Guidance literature:

Multi-step reaction with 5 steps

1: NEt₃, (PhO)2PON₃ / 17 h / Heating

2: NH₄OH / 5 h / 25 °C

3: NEt₃, DMAP / CH₂Cl₂ / 1) 0 deg C, 15 min, 2) 25 deg C, 3 h

4: TsCl, pyridine / 12 h / Heating

5: 35 h / 25 °C / Candida cylindracea, phosphate buffer pH 7.5

With pyridine; dmap; ammonium hydroxide; diphenyl phosphoryl azide; triethylamine; p-toluenesulfonyl chloride; In dichloromethane;

DOI:10.1021/jo00048a028

upstream raw materials:

(1R,2R)-(-)-1--2-<(hexanoyloxy)methyl>cyclopropane-1-carbonitrile

(1S,2S)-(+)-1--2-<(hexanoyloxy)methyl>cyclopropane-1-carbonitrile

(1S,5S)-1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo<3.1.0>hexane

(1S,5R)-1-carboxy-2-oxo-3-oxabicyclo[3.1.0]hexane

Downstream raw materials:

(E)-2,3-methanomethionine