3-Cyclohexene-1-carboxylic acid, 4-methyl-, (1R,5R,6R)-6-[(2,2-dimethyl-1-oxopropyl)amino]spiro[4.4]non-1-yl ester, (1R)-

Base Information

• Chemical Name: 3-Cyclohexene-1-carboxylic acid, 4-methyl-, (1R,5R,6R)-6-[(2,2-dimethyl-1-oxopropyl)amino]spiro[4.4]non-1-yl ester, (1R)-
• CAS No.: 575343-70-3
• Molecular Formula: C22H35NO3
• Molecular Weight: 361.525
• Mol file: 575343-70-3.mol

Synonyms:

Chemical Property of 3-Cyclohexene-1-carboxylic acid, 4-methyl-, (1R,5R,6R)-6-[(2,2-dimethyl-1-oxopropyl)amino]spiro[4.4]non-1-yl ester, (1R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Cyclohexene-1-carboxylic acid, 4-methyl-, (1R,5R,6R)-6-[(2,2-dimethyl-1-oxopropyl)amino]spiro[4.4]non-1-yl ester, (1R)-

There total 9 articles about 3-Cyclohexene-1-carboxylic acid, 4-methyl-, (1R,5R,6R)-6-[(2,2-dimethyl-1-oxopropyl)amino]spiro[4.4]non-1-yl ester, (1R)- 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: 78.0%

Acrylic acid (1R,5R,6R)-6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester (575343-07-6) + isoprene (78-79-5,9003-31-0) → (R)-4-Methyl-cyclohex-3-enecarboxylic acid (1R,5R,6R)-6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester (575343-70-3)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 ℃;

DOI:10.1016/S0957-4166(03)00051-X

Reference yield:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → (R)-4-Methyl-cyclohex-3-enecarboxylic acid (1R,5R,6R)-6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester (575343-70-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Mg; iodine / tetrahydrofuran / 24 h / Heating

1.2: tetrahydrofuran / 5 h / Heating

2.1: 17.8 g / oxalic acid / dimethylsulfoxide; H₂O / 2 h / 120 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

4.1: hydroxylamine hydrochloride; sodium carbonate / diethyl ether; H₂O / 15 h

5.1: 51.2 percent / NaOCl / CH₂Cl₂; H₂O / 15 h

6.1: 277 mg / lithium aluminum hydride / tetrahydrofuran / 15 h / 22 °C

7.1: 97 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

8.1: 74.5 percent / triethylamine / CH₂Cl₂ / 18 h / 20 °C

9.1: 78 percent / BCl₃ / CH₂Cl₂ / -78 °C

With pyridine; sodium hypochlorite; lithium aluminium tetrahydride; hydroxylamine hydrochloride; iodine; oxalic acid; boron trichloride; sodium carbonate; Dess-Martin periodane; magnesium; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; 9.1: Diels-Alder reaction;

DOI:10.1016/S0957-4166(03)00051-X

Reference yield:

1-(4-hydroxybutyl)cyclopentan-1-ol (52318-90-8) → (R)-4-Methyl-cyclohex-3-enecarboxylic acid (1R,5R,6R)-6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester (575343-70-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 17.8 g / oxalic acid / dimethylsulfoxide; H₂O / 2 h / 120 °C

2: Dess-Martin periodinane / CH₂Cl₂ / 1 h

3: hydroxylamine hydrochloride; sodium carbonate / diethyl ether; H₂O / 15 h

4: 51.2 percent / NaOCl / CH₂Cl₂; H₂O / 15 h

5: 277 mg / lithium aluminum hydride / tetrahydrofuran / 15 h / 22 °C

6: 97 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

7: 74.5 percent / triethylamine / CH₂Cl₂ / 18 h / 20 °C

8: 78 percent / BCl₃ / CH₂Cl₂ / -78 °C

With pyridine; sodium hypochlorite; lithium aluminium tetrahydride; hydroxylamine hydrochloride; oxalic acid; boron trichloride; sodium carbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; 8: Diels-Alder reaction;

DOI:10.1016/S0957-4166(03)00051-X

upstream raw materials:

Acrylic acid (1R,5R,6R)-6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester

isoprene

3,4,5,6-tetrahydro-2H-pyran-2-one

1-(4-hydroxybutyl)cyclopentan-1-ol

Downstream raw materials:

(+)-(1R)-4-methyl-cyclohex-3-enecarboxylic acid