(5SR,6RS,8SR,11RS)-6-benzyloxy-11-butyl-1-aza-3-oxatricyclo[6.3.0.0^5,11]undecane

Base Information

• Chemical Name: (5SR,6RS,8SR,11RS)-6-benzyloxy-11-butyl-1-aza-3-oxatricyclo[6.3.0.0^5,11]undecane
• CAS No.: 141936-98-3
• Molecular Formula: C₂₀H₂₉NO₂
• Molecular Weight: 315.456

Synonyms:(5SR,6RS,8SR,11RS)-6-benzyloxy-11-butyl-1-aza-3-oxatricyclo[6.3.0.0^5,11]undecane

Chemical Property of (5SR,6RS,8SR,11RS)-6-benzyloxy-11-butyl-1-aza-3-oxatricyclo[6.3.0.0^5,11]undecane

Chemical Property:

Purity/Quality:

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Technology Process of (5SR,6RS,8SR,11RS)-6-benzyloxy-11-butyl-1-aza-3-oxatricyclo[6.3.0.0^5,11]undecane

There total 4 articles about (5SR,6RS,8SR,11RS)-6-benzyloxy-11-butyl-1-aza-3-oxatricyclo[6.3.0.0^5,11]undecane 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: 75.0%

dimethyl (1RS,2RS,3RS,5SR)-3-benzyloxy-1-butyl-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate (141936-96-1) → (5SR,6RS,8SR,11RS)-6-benzyloxy-11-butyl-1-aza-3-oxatricyclo[6.3.0.05,11]undecane (141936-98-3) + (1RS,2SR,3RS,5SR)-3-benzyloxy-1-butyl-2-hydroxymethyl-8-methoxycarbonyl-8-azabicyclo[3.2.1]octane (141936-99-4)

Guidance literature:

With diisobutylaluminium hydride; In hexane; at -78 ℃; for 1h;

DOI:10.1039/c39920000538

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → (5SR,6RS,8SR,11RS)-6-benzyloxy-11-butyl-1-aza-3-oxatricyclo[6.3.0.05,11]undecane (141936-98-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / trifluoromethanesulfonic acid / cyclohexane; CH₂Cl₂ / 12 h / 20 °C

2: diisobutylaluminum hydride (DIBAL-H) / hexane / 1 h / -78 °C

With trifluorormethanesulfonic acid; diisobutylaluminium hydride; In hexane; dichloromethane; cyclohexane;

DOI:10.1039/c39920000538

Reference yield:

(1RS,2RS,5SR)-1-butyl-2,8-dimethoxycarbonyl-8-azabicyclo[3.2.1]octan-3-one (141936-93-8) → (5SR,6RS,8SR,11RS)-6-benzyloxy-11-butyl-1-aza-3-oxatricyclo[6.3.0.05,11]undecane (141936-98-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Zn(BH₄)2*Et₂O / 1 h / 0 °C

2: 95 percent / trifluoromethanesulfonic acid / cyclohexane; CH₂Cl₂ / 12 h / 20 °C

3: diisobutylaluminum hydride (DIBAL-H) / hexane / 1 h / -78 °C

With trifluorormethanesulfonic acid; Zn(BH₄)2*Et₂O; diisobutylaluminium hydride; In hexane; dichloromethane; cyclohexane;

DOI:10.1039/c39920000538

upstream raw materials:

dimethyl (1RS,2RS,3RS,5SR)-3-benzyloxy-1-butyl-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate

O-benzyl 2,2,2-trichloroacetimidate

(1RS,2RS,5SR)-1-butyl-2,8-dimethoxycarbonyl-8-azabicyclo[3.2.1]octan-3-one

dimethyl (1RS,2RS,3RS,5SR)-1-butyl-3-hydroxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate

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