(7,8-trans)-methyl 8-((2-(4-bromophenyl)-2-oxoethyl)carbamoyl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate

Base Information

• Chemical Name: (7,8-trans)-methyl 8-((2-(4-bromophenyl)-2-oxoethyl)carbamoyl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate
• CAS No.: 1445591-71-8
• Molecular Formula: C₁₈H₂₀BrNO₆
• Molecular Weight: 426.264
• Mol file: 1445591-71-8.mol

Synonyms:(7,8-trans)-methyl 8-((2-(4-bromophenyl)-2-oxoethyl)carbamoyl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate

Chemical Property of (7,8-trans)-methyl 8-((2-(4-bromophenyl)-2-oxoethyl)carbamoyl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7,8-trans)-methyl 8-((2-(4-bromophenyl)-2-oxoethyl)carbamoyl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate

There total 4 articles about (7,8-trans)-methyl 8-((2-(4-bromophenyl)-2-oxoethyl)carbamoyl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate 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: 63.0%

(7,8-trans)-8-(methoxycarbonyl)-1,4-dioxaspiro[4.4]nonane-7-carboxylic acid (1445591-69-4) + α-amino-4-bromoacetophenone hydrochloride (5467-72-1) → (7,8-trans)-methyl 8-((2-(4-bromophenyl)-2-oxoethyl)carbamoyl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate (1445591-71-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 5 ℃; for 0.0833333h;

Reference yield:

(1,2-trans)-1-benzyl 2-methyl 4-oxocyclopentane-1,2-dicarboxylate (1445591-65-0,164916-54-5) → (7,8-trans)-methyl 8-((2-(4-bromophenyl)-2-oxoethyl)carbamoyl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate (1445591-71-8)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / toluene / 2 h / Dean-Stark; Reflux

2: hydrogen; palladium 10% on activated carbon / methanol

3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 0 - 5 °C

With palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; N,N-dimethyl-formamide; toluene;

Reference yield:

(1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid (115694-82-1) → (7,8-trans)-methyl 8-((2-(4-bromophenyl)-2-oxoethyl)carbamoyl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate (1445591-71-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1,1'-carbonyldiimidazole / toluene / 0.67 h / 70 °C / Inert atmosphere

1.2: 4 h / 70 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / toluene / 2 h / Dean-Stark; Reflux

3.1: hydrogen; palladium 10% on activated carbon / methanol

4.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 0 - 5 °C

With palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(7,8-trans)-8-(methoxycarbonyl)-1,4-dioxaspiro[4.4]nonane-7-carboxylic acid

α-amino-4-bromoacetophenone hydrochloride

(1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid

(1,2-trans)-1-benzyl 2-methyl 4-oxocyclopentane-1,2-dicarboxylate

Downstream raw materials:

(7,8-trans)-methyl 8-(5-(4-bromophenyl)-1H-imidazol-2-yl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate

(S)-methyl 2-((7,8-trans)-8-(5-(4-bromophenyl)-1H-imidazol-2-yl)-1,4-dioxaspiro[4.4]nonane-7-carboxamido)-3-methylbutanoate