N-((1S,3R,4S,5R)-4-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine

Base Information

Chemical Name:N-((1S,3R,4S,5R)-4-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine
CAS No.:1146974-80-2
Molecular Formula:C₁₇H₂₃NO
Molecular Weight:257.376
Hs Code.:

Synonyms:N-((1S,3R,4S,5R)-4-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine

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Chemical Property of N-((1S,3R,4S,5R)-4-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine

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Technology Process of N-((1S,3R,4S,5R)-4-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine

There total 6 articles about N-((1S,3R,4S,5R)-4-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine 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:

: (1R,5R)-2-benzylidene-7-methylenebicyclo[3.3.1]nonan-3-one

: 1146974-80-2
N-((1S,3R,4S,5R)-4-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine

: 1146974-46-0
N-((1R,2S,3R,5R)-2-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine

Guidance literature:: (1R,5R)-2-benzylidene-7-methylenebicyclo[3.3.1]nonan-3-one; With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 12h;

With pyridine; hydroxylamine hydrochloride; at 20 ℃; for 3h; Inert atmosphere;

With ethanol; sodium cyanoborohydride; trifluoroacetic acid; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol900441f

Reference yield:

: 100-52-7
benzaldehyde

: 1146974-80-2
N-((1S,3R,4S,5R)-4-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine

: 1146974-46-0
N-((1R,2S,3R,5R)-2-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine

Guidance literature:: Multi-step reaction with 4 steps

1.1: (R,R)-N,N-bis-(1-phenylethyl)amine; n-butyllithium; lithium chloride / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / 50 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / ethanol / 12 h / 20 °C

4.2: 3 h / 20 °C / Inert atmosphere

4.3: 2 h / 0 °C / Inert atmosphere

With n-butyllithium; palladium 10% on activated carbon; hydrogen; (R,R)-N,N-bis-(1-phenylethyl)amine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene;
DOI:10.1021/ja509766f

Reference yield:

: Methanesulfonic acid (R)-((1R,2S,5S)-7-methylene-3-oxo-bicyclo[3.3.1]non-2-yl)-phenyl-methyl ester

: 1146974-80-2
N-((1S,3R,4S,5R)-4-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine

: 1146974-46-0
N-((1R,2S,3R,5R)-2-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / 50 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / ethanol / 12 h / 20 °C

2.2: 3 h / 20 °C / Inert atmosphere

2.3: 2 h / 0 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; toluene;
DOI:10.1021/ja509766f