4-exo-hydroxy-3-endo-methoxy-6-<((R)-1-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)

Base Information

Chemical Name:4-exo-hydroxy-3-endo-methoxy-6-<((R)-1-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)
CAS No.:116233-63-7
Molecular Formula:C₁₆H₂₁NO₅
Molecular Weight:307.346
Hs Code.:

Synonyms:4-exo-hydroxy-3-endo-methoxy-6-<((R)-1-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)

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Chemical Property of 4-exo-hydroxy-3-endo-methoxy-6-<((R)-1-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)

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Technology Process of 4-exo-hydroxy-3-endo-methoxy-6-<((R)-1-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)

There total 14 articles about 4-exo-hydroxy-3-endo-methoxy-6-<((R)-1-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D) 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: 92.0%

: 67-56-1
methanol

: 116233-62-6
6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo-<3.2.1>oct-3-en-7-one

: 116233-63-7
4-exo-hydroxy-3-endo-methoxy-6-<((R)-1-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; at 23 ℃; for 12h;
DOI:10.1021/jo00255a020

Reference yield:

: 116233-54-6
3,6-dihydro-2H-pyran-2-carboxylic acid

: 116233-63-7
4-exo-hydroxy-3-endo-methoxy-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (L)

Guidance literature:: Multi-step reaction with 6 steps

1: oxalyl chloride / toluene / 0.5 h

2: Et₃N / toluene / 23 °C

3: pentane / 1 h

4: Br(coll)2ClO₄ (bromonium bis(collidine) perchlorate) / CH₂Cl₂ / 1.) 5 min. -78 deg C; 2.) from -78 deg C to RT

5: 100 mg / potassium tert-butoxide / dimethylsulfoxide / 12 h / 23 °C

6: m-chloroperbenzoic acid (mCPBA) / 12 h / 23 °C

With oxalyl dichloride; bromonium bis(collidine) perchlorate; potassium tert-butylate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; dimethyl sulfoxide; toluene; pentane;
DOI:10.1021/jo00255a020

Reference yield:

: 116233-54-6
3,6-dihydro-2H-pyran-2-carboxylic acid

: 116233-63-7
4-exo-hydroxy-3-endo-methoxy-6-<((R)-1-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D)

Guidance literature:: Multi-step reaction with 6 steps

1: oxalyl chloride / toluene / 0.5 h

2: Et₃N / toluene / 23 °C

3: pentane / 1 h

4: Br(coll)2ClO₄ (bromonium bis(collidine) perchlorate) / CH₂Cl₂ / 1.) 5 min. -78 deg C; 2.) from -78 deg C to RT

5: 290 mg / potassium tert-butoxide / dimethylsulfoxide / 12 h / 23 °C

6: 92 percent / m-chloroperbenzoic acid (mCPBA) / 12 h / 23 °C

With oxalyl dichloride; bromonium bis(collidine) perchlorate; potassium tert-butylate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; dimethyl sulfoxide; toluene; pentane;
DOI:10.1021/jo00255a020