(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone

Base Information

Chemical Name:(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone
CAS No.:168773-42-0
Molecular Formula:C₁₉H₂₉NO₂Si
Molecular Weight:331.53
Hs Code.:

Synonyms:(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone

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Chemical Property of (1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone

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Technology Process of (1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone

There total 10 articles about (1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone 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%

: 168773-45-3
(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone

: 168773-42-0
(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min;
DOI:10.1021/jo00119a044

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 168773-42-0
(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / dimethylformamide / 15 h

2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h

3: 100 percent / H₂ / 10percent Pd/C / ethanol / 23 h

4: 93 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h

5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min

With 1H-imidazole; carbon tetrabromide; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00119a044

Reference yield:

: 100-39-0
benzyl bromide

: 168773-42-0
(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h

2: 100 percent / H₂ / 10percent Pd/C / ethanol / 23 h

3: 93 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h

4: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min

With carbon tetrabromide; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jo00119a044