tert-butyl (5S,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate

Base Information

• Chemical Name: tert-butyl (5S,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate
• CAS No.: 453524-69-1
• Molecular Formula: C₂₃H₃₂N₂O₆
• Molecular Weight: 432.517

Synonyms:tert-butyl (5S,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate

Chemical Property of tert-butyl (5S,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate

Chemical Property:

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Technology Process of tert-butyl (5S,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate

There total 2 articles about tert-butyl (5S,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-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:

p-methoxyl benzaldoxime (3717-21-3,3717-22-4,140461-28-5,140461-29-6,3235-04-9) + tert-Butyl (2S)-N-tert-butoxycarbonyl-4-methylideneprolinate (163190-46-3) → tert-butyl (5R,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate (453524-68-0) + tert-butyl (5S,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate (453524-69-1)

Guidance literature:

With sodium hypochlorite; In dichloromethane; at 0 - 20 ℃; for 8h;

DOI:10.1021/jo025611j

Reference yield:

(S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid (84348-38-9,1427175-11-8) → tert-butyl (5S,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate (453524-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-(dimethylamino)pyridine; N,N-dicyclohexylcarbodiimide / CH₂Cl₂ / 0 - 20 °C

2: aq. NaOCl / CH₂Cl₂ / 8 h / 0 - 20 °C

With dmap; sodium hypochlorite; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo025611j

Reference yield: 92.0%

tert-butyl (5S,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate (453524-69-1) → (5S,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylic acid (453524-76-0)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 6h; Heating;

DOI:10.1021/jo025611j

upstream raw materials:

p-methoxyl benzaldoxime

tert-Butyl (2S)-N-tert-butoxycarbonyl-4-methylideneprolinate

(S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid

Downstream raw materials:

(5S,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylic acid

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