(3aR,7aR)-3-Benzyl-3a-((R)-hydroxy-pyridin-3-yl-methyl)-hexahydro-benzooxazol-2-one

Base Information

• Chemical Name: (3aR,7aR)-3-Benzyl-3a-((R)-hydroxy-pyridin-3-yl-methyl)-hexahydro-benzooxazol-2-one
• CAS No.: 142968-24-9
• Molecular Formula: C₂₀H₂₂N₂O₃
• Molecular Weight: 338.406

Synonyms:(3aR,7aR)-3-Benzyl-3a-((R)-hydroxy-pyridin-3-yl-methyl)-hexahydro-benzooxazol-2-one

Chemical Property of (3aR,7aR)-3-Benzyl-3a-((R)-hydroxy-pyridin-3-yl-methyl)-hexahydro-benzooxazol-2-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (3aR,7aR)-3-Benzyl-3a-((R)-hydroxy-pyridin-3-yl-methyl)-hexahydro-benzooxazol-2-one

There total 6 articles about (3aR,7aR)-3-Benzyl-3a-((R)-hydroxy-pyridin-3-yl-methyl)-hexahydro-benzooxazol-2-one 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: 40.0%

Benzyl-carbamic acid (2S,3S,4S)-2-pyridin-3-yl-1-oxa-spiro[2.5]oct-4-yl ester (142968-20-5) → (4S,4aS,8aR)-3-Benzyl-4a-hydroxy-4-pyridin-3-yl-octahydro-benzo[e][1,3]oxazin-2-one (142968-22-7) + (3aR,7aR)-3-Benzyl-3a-((R)-hydroxy-pyridin-3-yl-methyl)-hexahydro-benzooxazol-2-one (142968-24-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 25 ℃; Yield given;

DOI:10.1016/S0040-4039(00)79585-2

Reference yield:

2-[1-Pyridin-3-yl-meth-(E)-ylidene]-cyclohexanone (142968-16-9) → (3aR,7aR)-3-Benzyl-3a-((R)-hydroxy-pyridin-3-yl-methyl)-hexahydro-benzooxazol-2-one (142968-24-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / H₂O₂, NaOH / methanol / 0 - 5 °C

2: 95 percent / KBH₄ / ethanol; CH₂Cl₂ / -15 °C

3: NEt₃ / CH₂Cl₂ / 25 °C

4: 40 percent / NaH / tetrahydrofuran / 25 °C

With sodium hydroxide; potassium borohydride; dihydrogen peroxide; sodium hydride; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)79585-2

Reference yield:

(2S,3S,4S)-2-Pyridin-3-yl-1-oxa-spiro[2.5]octan-4-ol (142968-18-1) → (3aR,7aR)-3-Benzyl-3a-((R)-hydroxy-pyridin-3-yl-methyl)-hexahydro-benzooxazol-2-one (142968-24-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NEt₃ / CH₂Cl₂ / 25 °C

2: 40 percent / NaH / tetrahydrofuran / 25 °C

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)79585-2

upstream raw materials:

Benzyl-carbamic acid (2S,3S,4S)-2-pyridin-3-yl-1-oxa-spiro[2.5]oct-4-yl ester

2-[1-Pyridin-3-yl-meth-(E)-ylidene]-cyclohexanone

(2S,3S,4S)-2-Pyridin-3-yl-1-oxa-spiro[2.5]octan-4-ol

(2S,3R)-2-Pyridin-3-yl-1-oxa-spiro[2.5]octan-4-one

Downstream raw materials:

(1S,2R)-2-Benzylamino-2-((S)-hydroxy-pyridin-3-yl-methyl)-cyclohexanol

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