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

Base Information

• Chemical Name: dimethyl (1RS,2RS,3RS,5SR)-3-benzyloxy-1-butyl-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate
• CAS No.: 141936-96-1
• Molecular Formula: C₂₂H₃₁NO₅
• Molecular Weight: 389.492

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

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

Chemical Property:

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

There total 2 articles about dimethyl (1RS,2RS,3RS,5SR)-3-benzyloxy-1-butyl-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate 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: 99.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + dimethyl (1RS,2RS,3RS,5SR)-1-butyl-3-hydroxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate (141936-95-0,142034-00-2) → dimethyl (1RS,2RS,3RS,5SR)-3-benzyloxy-1-butyl-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate (141936-96-1)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; at 20 ℃; for 12h;

DOI:10.1039/b708910d

Reference yield:

(1RS,2RS,5SR)-1-butyl-2,8-dimethoxycarbonyl-8-azabicyclo[3.2.1]octan-3-one (141936-93-8) → dimethyl (1RS,2RS,3RS,5SR)-3-benzyloxy-1-butyl-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate (141936-96-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Zn(BH₄)2*Et₂O / 1 h / 0 °C

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

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

DOI:10.1039/c39920000538

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) → (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/b708910d

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

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

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

Downstream raw materials:

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

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

(4RS,5RS,7SR,10RS)-5-benzyloxy-10-butyl-1-azatricyclo[5.3.0.0^4,10]decan-2-ol

(4RS,5RS,7SR,10RS)-5-benzyloxy-10-butyl-1-azatricyclo[5.3.0.0^4,10]decan-2-one

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