(3aS,6R,7aS)-8,8-dimethyl-1-{(2S)-4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-(phenylmethyl)butanoyl}hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide

Base Information

• Chemical Name: (3aS,6R,7aS)-8,8-dimethyl-1-{(2S)-4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-(phenylmethyl)butanoyl}hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide
• CAS No.: 787635-24-9
• Molecular Formula: C₂₉H₄₀N₂O₄S
• Molecular Weight: 512.714
• Mol file: 787635-24-9.mol

Synonyms:(3aS,6R,7aS)-8,8-dimethyl-1-{(2S)-4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-(phenylmethyl)butanoyl}hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide

Chemical Property of (3aS,6R,7aS)-8,8-dimethyl-1-{(2S)-4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-(phenylmethyl)butanoyl}hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3aS,6R,7aS)-8,8-dimethyl-1-{(2S)-4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-(phenylmethyl)butanoyl}hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide

There total 7 articles about (3aS,6R,7aS)-8,8-dimethyl-1-{(2S)-4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-(phenylmethyl)butanoyl}hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 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: 85.0%

1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-phenylpropan-1-one (127392-81-8) + (3aR,7aS)-2-(bromoacetyl)octahydro-1H-isoindole (787635-25-0) → (3aS,6R,7aS)-8,8-dimethyl-1-{(2S)-4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-(phenylmethyl)butanoyl}hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide (787635-24-9)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃; for 16h;

DOI:10.1002/hlca.200490174

Reference yield: 84.0%

cis-hexahydroisoindoline (1470-99-1,1220913-24-5) + (3S)-4-[(3aS,6R,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-4-oxo-3-(phenylmethyl)butanoic acid (787635-23-8) → (3aS,6R,7aS)-8,8-dimethyl-1-{(2S)-4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-(phenylmethyl)butanoyl}hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide (787635-24-9)

Guidance literature:

With 4-methyl-morpholine; pivaloyl chloride; In tetrahydrofuran; at -12 ℃;

DOI:10.1002/hlca.200490174

Reference yield:

hydrocinnamic acid chloride (645-45-4) → (3aS,6R,7aS)-8,8-dimethyl-1-{(2S)-4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-(phenylmethyl)butanoyl}hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide (787635-24-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 91 percent / NaH / toluene / 20 °C

2.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: hexamethylphosphoramide (HMPA) / tetrahydrofuran / 16 h / -78 °C

2.3: 92 percent / tetrahydrofuran / 4 h / 20 °C

3.1: 87 percent / CF₃COOH / CH₂Cl₂ / 20 °C

4.1: 84 percent / 4-methylmorpholine (NMM); ClCOtBu / tetrahydrofuran / -12 °C

With 4-methyl-morpholine; sodium hexamethyldisilazane; pivaloyl chloride; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/hlca.200490174

upstream raw materials:

cis-hexahydroisoindoline

(3S)-4-[(3aS,6R,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-4-oxo-3-(phenylmethyl)butanoic acid

1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-phenylpropan-1-one

(3aR,7aS)-2-(bromoacetyl)octahydro-1H-isoindole

Downstream raw materials:

mitiglinide