(-)-(1R,5S,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4,8-dione

Base Information

Chemical Name:(-)-(1R,5S,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4,8-dione
CAS No.:139068-96-5
Molecular Formula:C₁₈H₂₃NO₂
Molecular Weight:285.386
Hs Code.:

Synonyms:(-)-(1R,5S,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4,8-dione

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Chemical Property of (-)-(1R,5S,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4,8-dione

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Technology Process of (-)-(1R,5S,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4,8-dione

There total 12 articles about (-)-(1R,5S,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4,8-dione 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: 22.0%

: 139025-19-7
(-)-(1S,2S,6R,7S,9R,1'S)-2,7-dimethyl-4-(1'-phenylethyl)-4-azatricyclo<4.3.0.0^2.9>nonan-3,8-dione

: 139068-96-5
(-)-(1R,5S,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4,8-dione

: 139025-20-0
(-)-(1R,5R,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4,8-dione

Guidance literature:: With zinc; In acetic acid; for 20h; Heating;
DOI:10.1002/hlca.19930760416

Reference yield:

: 139025-15-3,139069-01-5
(1S,6R,1'S)-5-methyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>non-7-en-4-one

: 139068-96-5
(-)-(1R,5S,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4,8-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 3-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / -18 °C

2: 1) Et₂NH, BuLi / 1) Et₂O, hexane, ice-bath, 10 min, 2) Et₂O, r.t., overnight

3: 1) DMSO, oxalyl chloride, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 45 min, 2) CH₂Cl₂, -50 to -60 deg C, 45 min

4: 90 percent / HMPA, LDA / tetrahydrofuran / 2 h / -80 - -30 °C

5: 51 percent / Zn / acetic acid / 20 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; sodium hydrogencarbonate; dimethyl sulfoxide; diethylamine; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetic acid;
DOI:10.1002/hlca.19930760416

Reference yield:

: 139025-16-4
(-)-(1S,5R,6R,7R,8S,1'S)-7,8-epoxy-5-methyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4-one

: 139068-96-5
(-)-(1R,5S,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4,8-dione

Guidance literature:: Multi-step reaction with 4 steps

1: 1) Et₂NH, BuLi / 1) Et₂O, hexane, ice-bath, 10 min, 2) Et₂O, r.t., overnight

2: 1) DMSO, oxalyl chloride, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 45 min, 2) CH₂Cl₂, -50 to -60 deg C, 45 min

3: 90 percent / HMPA, LDA / tetrahydrofuran / 2 h / -80 - -30 °C

4: 51 percent / Zn / acetic acid / 20 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; diethylamine; triethylamine; zinc; lithium diisopropyl amide; In tetrahydrofuran; acetic acid;
DOI:10.1002/hlca.19930760416