(1R,4S,5S,6S)-2-benzyl-5,6-bis-(tert-butyldimethylsilanyloxy)-2-azabicyclo[2.2.1]-heptan-3-one

Base Information

Chemical Name:(1R,4S,5S,6S)-2-benzyl-5,6-bis-(tert-butyldimethylsilanyloxy)-2-azabicyclo[2.2.1]-heptan-3-one
CAS No.:445469-18-1
Molecular Formula:C₂₅H₄₃NO₃Si₂
Molecular Weight:461.792
Hs Code.:

Synonyms:(1R,4S,5S,6S)-2-benzyl-5,6-bis-(tert-butyldimethylsilanyloxy)-2-azabicyclo[2.2.1]-heptan-3-one

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Chemical Property of (1R,4S,5S,6S)-2-benzyl-5,6-bis-(tert-butyldimethylsilanyloxy)-2-azabicyclo[2.2.1]-heptan-3-one

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Technology Process of (1R,4S,5S,6S)-2-benzyl-5,6-bis-(tert-butyldimethylsilanyloxy)-2-azabicyclo[2.2.1]-heptan-3-one

There total 6 articles about (1R,4S,5S,6S)-2-benzyl-5,6-bis-(tert-butyldimethylsilanyloxy)-2-azabicyclo[2.2.1]-heptan-3-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: 78.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 445469-17-0
(2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde

: 872174-13-5
(1R,4S,5R,6S)-2-benzyl-5,6-bis-(tert-butyldimethylsilanyloxy)-2-azabicyclo[2.2.1]-heptan-3-one

: 445469-18-1
(1R,4S,5S,6S)-2-benzyl-5,6-bis-(tert-butyldimethylsilanyloxy)-2-azabicyclo[2.2.1]-heptan-3-one

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jm050698x

Reference yield:

: 141293-15-4
(1'S,2R,4''R)-2-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester

: 445469-18-1
(1R,4S,5S,6S)-2-benzyl-5,6-bis-(tert-butyldimethylsilanyloxy)-2-azabicyclo[2.2.1]-heptan-3-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / H₂; NaOAc / Pd/C / ethyl acetate / 24 h / 20 °C

2.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 20 °C

3.1: 93 percent / ammonium cerium(IV) nitrate / acetonitrile / 4 h / 80 °C

4.1: NaH / tetrahydrofuran / 0.17 h / 20 °C

4.2: 91 percent / tetrahydrofuran / 1.5 h / Heating

5.1: 98 percent / H₂IO₆ / ethyl acetate / 1 h / 20 °C

6.1: 78 percent / diisopropylethyl amine / CH₂Cl₂ / 2 h / 20 °C

With 2,6-dimethylpyridine; ammonium cerium(IV) nitrate; hydrogen; sodium acetate; sodium hydride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jm050698x

Reference yield:

: 872174-12-4
(1'S,4''R,5R)-5-[(tert-butyldimethylsilanyloxy)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]pyrrolidin-2-one

: 445469-18-1
(1R,4S,5S,6S)-2-benzyl-5,6-bis-(tert-butyldimethylsilanyloxy)-2-azabicyclo[2.2.1]-heptan-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0.17 h / 20 °C

1.2: 91 percent / tetrahydrofuran / 1.5 h / Heating

2.1: 98 percent / H₂IO₆ / ethyl acetate / 1 h / 20 °C

3.1: 78 percent / diisopropylethyl amine / CH₂Cl₂ / 2 h / 20 °C

With sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/jm050698x