(-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-7-one oxime

Base Information

Chemical Name:(-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-7-one oxime
CAS No.:444904-14-7
Molecular Formula:C₂₇H₃₆N₂O₂
Molecular Weight:420.595
Hs Code.:

Synonyms:(-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-7-one oxime

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Chemical Property of (-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-7-one oxime

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Technology Process of (-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-7-one oxime

There total 9 articles about (-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-7-one oxime 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: 90.0%

: 444904-11-4
(1R,4S,5R)-5-(3-Isopropoxy-phenyl)-4-methyl-2-(3-phenyl-propyl)-2-aza-bicyclo[3.3.1]nonan-7-one

: 444904-14-7
(-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-7-one oxime

Guidance literature:: With hydroxylamine hydrochloride; In ethanol; for 3h; Heating;
DOI:10.1021/jm020084h

Reference yield:

: 104-53-0
3-phenyl-propionaldehyde

: 444904-14-7
(-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-7-one oxime

Guidance literature:: Multi-step reaction with 3 steps

1: NaBH(OAc)3 / 1,2-dichloro-ethane / 24 h

2: 91 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -20 °C

3: 90 percent / HONH₂*HCl / ethanol / 3 h / Heating

With oxalyl dichloride; hydroxylamine hydrochloride; sodium tris(acetoxy)borohydride; dimethyl sulfoxide; triethylamine; In ethanol; dichloromethane; 1,2-dichloro-ethane; 2: Swern oxidation;
DOI:10.1021/jm020084h

Reference yield:

: 444904-02-3
(S)-1,2,3,6-tetrahydro-1,3-dimethyl-4-[3-(1-methylethoxy)phenyl]pyridine

: 444904-14-7
(-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-7-one oxime

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -10 °C

1.2: tetrahydrofuran; hexane / 2 h / -78 °C

1.3: 70 percent / 1 N aq. HCl / methanol / 20 °C

2.1: 95 percent / NaBH₄ / ethanol / 24 h / 20 °C

3.1: Et₃N; N,N-dimethylaminopyridine / CH₂Cl₂ / 20 °C

4.1: 1,2-dichloro-ethane / 2.5 h / Heating

5.1: aq. LiOH / methanol / Heating

6.1: NaBH(OAc)3 / 1,2-dichloro-ethane / 24 h

7.1: 91 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -20 °C

8.1: 90 percent / HONH₂*HCl / ethanol / 3 h / Heating

With dmap; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; hydroxylamine hydrochloride; sodium tris(acetoxy)borohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 1,2-dichloro-ethane; 7.1: Swern oxidation;
DOI:10.1021/jm020084h