6a-phenyl-2-o-tolyl-hexahydro-1-oxa-2a-aza-2-bora-cyclopenta[cd]pentalene

Base Information

• Chemical Name: 6a-phenyl-2-o-tolyl-hexahydro-1-oxa-2a-aza-2-bora-cyclopenta[cd]pentalene
• CAS No.: 705284-28-2
• Molecular Formula: C₂₀H₂₂BNO
• Molecular Weight: 303.212

Synonyms:6a-phenyl-2-o-tolyl-hexahydro-1-oxa-2a-aza-2-bora-cyclopenta[cd]pentalene

Chemical Property of 6a-phenyl-2-o-tolyl-hexahydro-1-oxa-2a-aza-2-bora-cyclopenta[cd]pentalene

Chemical Property:

Purity/Quality:

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Technology Process of 6a-phenyl-2-o-tolyl-hexahydro-1-oxa-2a-aza-2-bora-cyclopenta[cd]pentalene

There total 6 articles about 6a-phenyl-2-o-tolyl-hexahydro-1-oxa-2a-aza-2-bora-cyclopenta[cd]pentalene 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:

phenyllithium (591-51-5) → 6a-phenyl-2-o-tolyl-hexahydro-1-oxa-2a-aza-2-bora-cyclopenta[cd]pentalene (705284-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / tetrahydrofuran

2: 93 percent / H₂; AcOH / Pd(OH)2/C / methanol / 2 h / 20 °C / 760 Torr

3: 4 Angstroem molecular sieves / toluene / 4 h / Heating

With 4 A molecular sieve; hydrogen; acetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; toluene;

DOI:10.1021/ja048808x

Reference yield:

(3aS,6aR)-1-Benzyl-6-bromo-octahydro-cyclopenta[b]pyrrole → 6a-phenyl-2-o-tolyl-hexahydro-1-oxa-2a-aza-2-bora-cyclopenta[cd]pentalene (705284-28-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 593 mg / aq. LiOH / 1,2-dimethoxy-ethane / Heating

2: 91 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3: 87 percent / tetrahydrofuran

4: 93 percent / H₂; AcOH / Pd(OH)2/C / methanol / 2 h / 20 °C / 760 Torr

5: 4 Angstroem molecular sieves / toluene / 4 h / Heating

With lithium hydroxide; oxalyl dichloride; 4 A molecular sieve; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; toluene; 2: Swern oxidation;

DOI:10.1021/ja048808x

Reference yield:

(3aS,6aR)-1-Benzyl-hexahydro-cyclopenta[b]pyrrol-6-one (705284-41-9) → 6a-phenyl-2-o-tolyl-hexahydro-1-oxa-2a-aza-2-bora-cyclopenta[cd]pentalene (705284-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / tetrahydrofuran

2: 93 percent / H₂; AcOH / Pd(OH)2/C / methanol / 2 h / 20 °C / 760 Torr

3: 4 Angstroem molecular sieves / toluene / 4 h / Heating

With 4 A molecular sieve; hydrogen; acetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; toluene;

DOI:10.1021/ja048808x

upstream raw materials:

tri-o-tolylboroxine

(3aS,6R,6aR)-6-Phenyl-octahydro-cyclopenta[b]pyrrol-6-ol

phenyllithium

(3aS,6R,6aR)-1-Benzyl-octahydro-cyclopenta[b]pyrrol-6-ol

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