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

Base Information

Chemical Name:(1RS,2RS,3RS,5SR)-3-benzyloxy-1-butyl-2-methoxycarbonylmethyl-8-azabicyclo[3.2.1]octane
CAS No.:141937-06-6
Molecular Formula:C₂₁H₃₁NO₃
Molecular Weight:345.482
Hs Code.:

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

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

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

There total 6 articles about (1RS,2RS,3RS,5SR)-3-benzyloxy-1-butyl-2-methoxycarbonylmethyl-8-azabicyclo[3.2.1]octane 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: 86.0%

: 141937-01-1
(1RS,2RS,3RS,5SR)-3-benzyloxy-1-butyl-2-iodomethyl-8-methoxycarbonyl-8-azabicyclo[3.2.1]octane

: 141937-03-3
(4RS,5RS,7SR,10RS)-5-benzyloxy-10-butyl-1-azatricyclo[5.3.0.0^4,10]decan-2-one

: 141937-06-6
(1RS,2RS,3RS,5SR)-3-benzyloxy-1-butyl-2-methoxycarbonylmethyl-8-azabicyclo[3.2.1]octane

Guidance literature:: With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1039/c39920000538

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 141937-06-6
(1RS,2RS,3RS,5SR)-3-benzyloxy-1-butyl-2-methoxycarbonylmethyl-8-azabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 4 steps

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

2: 75 percent / diisobutylaluminum hydride (DIBAL-H) / hexane / 1 h / -78 °C

3: 71 percent / I₂, PPh₃, imidazole / CH₂Cl₂ / 3 h

4: 70 percent / tert-butyllithium / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; trifluorormethanesulfonic acid; iodine; tert.-butyl lithium; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; cyclohexane;
DOI:10.1039/c39920000538

Reference yield:

: 141936-93-8
(1RS,2RS,5SR)-1-butyl-2,8-dimethoxycarbonyl-8-azabicyclo[3.2.1]octan-3-one

: 141937-06-6
(1RS,2RS,3RS,5SR)-3-benzyloxy-1-butyl-2-methoxycarbonylmethyl-8-azabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 5 steps

1: Zn(BH₄)2*Et₂O / 1 h / 0 °C

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

3: 75 percent / diisobutylaluminum hydride (DIBAL-H) / hexane / 1 h / -78 °C

4: 71 percent / I₂, PPh₃, imidazole / CH₂Cl₂ / 3 h

5: 70 percent / tert-butyllithium / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; trifluorormethanesulfonic acid; Zn(BH₄)2*Et₂O; iodine; tert.-butyl lithium; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; cyclohexane;
DOI:10.1039/c39920000538