N-[(R)-α-(hydroxymethyl)benzyl]-(1R,2S)-cis-2-methylcyclobutanecarboxamide

Base Information

• Chemical Name: N-[(R)-α-(hydroxymethyl)benzyl]-(1R,2S)-cis-2-methylcyclobutanecarboxamide
• CAS No.: 301824-29-3
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.31
• Mol file: 301824-29-3.mol

Synonyms:

Chemical Property of N-[(R)-α-(hydroxymethyl)benzyl]-(1R,2S)-cis-2-methylcyclobutanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(R)-α-(hydroxymethyl)benzyl]-(1R,2S)-cis-2-methylcyclobutanecarboxamide

There total 10 articles about N-[(R)-α-(hydroxymethyl)benzyl]-(1R,2S)-cis-2-methylcyclobutanecarboxamide 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:

cis-3-cyclobutene-1,2-dicarboxylic anhydride → N-[(R)-α-(hydroxymethyl)benzyl]-(1R,2S)-cis-2-methylcyclobutanecarboxamide (301824-29-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 82 percent / NaBH₄ / tetrahydrofuran

2.1: 89 percent / H₂ / Pd/C / diethyl ether / 4 h

3.1: HBr / -78 - 20 °C

4.1: 0.67 g / NaBH₄ / hexamethylphosphoric acid triamide / 3 h / 0 - 20 °C

5.1: 91 percent / H₂SO₄ / tetrahydrofuran; H₂O / 23 h / Heating

6.1: NaH / CH₂Cl₂ / 0 - 20 °C

6.2: (COCl)2; DMF / CH₂Cl₂ / 2.5 h / 0 - 20 °C

7.1: 1,8-bis(dimethylamino)naphthalene / CH₂Cl₂ / -78 - 20 °C

7.2: 300 mg / HCl / CH₂Cl₂; H₂O / 1 h

With sodium tetrahydroborate; sulfuric acid; hydrogen bromide; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; 1.1: Reduction / 2.1: Catalytic hydrogenation / 3.1: Ring cleavage / 4.1: Reduction / 5.1: Hydrolysis / 6.1: Metallation / 6.2: Substitution / 7.1: Condensation / 7.2: Hydrolysis;

DOI:10.1021/jo0009550

Reference yield:

2-oxo-3-oxabicyclo<3.2.0>-6-heptene → N-[(R)-α-(hydroxymethyl)benzyl]-(1R,2S)-cis-2-methylcyclobutanecarboxamide (301824-29-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 89 percent / H₂ / Pd/C / diethyl ether / 4 h

2.1: HBr / -78 - 20 °C

3.1: 0.67 g / NaBH₄ / hexamethylphosphoric acid triamide / 3 h / 0 - 20 °C

4.1: 91 percent / H₂SO₄ / tetrahydrofuran; H₂O / 23 h / Heating

5.1: NaH / CH₂Cl₂ / 0 - 20 °C

5.2: (COCl)2; DMF / CH₂Cl₂ / 2.5 h / 0 - 20 °C

6.1: 1,8-bis(dimethylamino)naphthalene / CH₂Cl₂ / -78 - 20 °C

6.2: 300 mg / HCl / CH₂Cl₂; H₂O / 1 h

With sodium tetrahydroborate; sulfuric acid; hydrogen bromide; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; 1.1: Catalytic hydrogenation / 2.1: Ring cleavage / 3.1: Reduction / 4.1: Hydrolysis / 5.1: Metallation / 5.2: Substitution / 6.1: Condensation / 6.2: Hydrolysis;

DOI:10.1021/jo0009550

Reference yield:

cis-2-methylcyclobutanecarboxylic acid chloride + (R)-1-Phenyl-2-trimethylsilanyloxy-ethylamine → N-[(R)-α-(hydroxymethyl)benzyl]-(1R,2S)-cis-2-methylcyclobutanecarboxamide (301824-29-3) + (1S,2R)-2-Methyl-cyclobutanecarboxylic acid ((R)-2-hydroxy-1-phenyl-ethyl)-amide (301824-30-6)

Guidance literature:

cis-2-methylcyclobutanecarboxylic acid chloride; (R)-1-Phenyl-2-trimethylsilanyloxy-ethylamine; With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; In dichloromethane; at -78 - 20 ℃;

With hydrogenchloride; In dichloromethane; water; for 1h; Further stages.;

DOI:10.1021/jo0009550

upstream raw materials:

2-methylcyclobutane-1-carboxylic acid

D-2-phenylglycinol

diethyl 2-methylcyclobutane-1,1-dicarboxylate

(+/-)-cis-3-oxabicyclo<3.2.0>heptan-2-one

Refernces