(+)-(1R,5S)-1-(acetoxymethyl)-3-benzyl-5-formyl-9-methylene-3-azabicyclo<3.3.1>nonane

Base Information

Chemical Name:(+)-(1R,5S)-1-(acetoxymethyl)-3-benzyl-5-formyl-9-methylene-3-azabicyclo<3.3.1>nonane
CAS No.:124097-11-6
Molecular Formula:C₂₀H₂₅NO₃
Molecular Weight:327.423
Hs Code.:

Synonyms:(+)-(1R,5S)-1-(acetoxymethyl)-3-benzyl-5-formyl-9-methylene-3-azabicyclo<3.3.1>nonane

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Chemical Property of (+)-(1R,5S)-1-(acetoxymethyl)-3-benzyl-5-formyl-9-methylene-3-azabicyclo<3.3.1>nonane

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Technology Process of (+)-(1R,5S)-1-(acetoxymethyl)-3-benzyl-5-formyl-9-methylene-3-azabicyclo<3.3.1>nonane

There total 4 articles about (+)-(1R,5S)-1-(acetoxymethyl)-3-benzyl-5-formyl-9-methylene-3-azabicyclo<3.3.1>nonane 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: 71.0%

: 124097-07-0
(-)-(1R,5S)-1-(acetoxymethyl)-3-benzyl-5-hydroxymethyl-9-methylene-3-azabicyclo<3.3.1>nonane

: 124097-11-6
(+)-(1R,5S)-1-(acetoxymethyl)-3-benzyl-5-formyl-9-methylene-3-azabicyclo<3.3.1>nonane

Guidance literature:: With dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 0.333333h;
DOI:10.1021/ja00159a042

Reference yield:

: 113161-22-1
dimethyl 3-benzyl-9-methylene-3-azabicyclo<3.3.1>nonane-1,5-dicarboxylate

: 124097-11-6
(+)-(1R,5S)-1-(acetoxymethyl)-3-benzyl-5-formyl-9-methylene-3-azabicyclo<3.3.1>nonane

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

2: 1 percent / Candidia cylindracea lipase-type VII / benzene / 11 h / 28 °C

3: Celite, Candida cylindracea lipase-type VII / 2,2,4-trimethyl-pentane; H₂O / 48 h / 35 °C

4: 71 percent / COCl₂, DMSO, Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

With lithium aluminium tetrahydride; Candida cylindracea lipase-type VII; Candidia cylindracea lipase-type VII; Celite; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; water; benzene;
DOI:10.1021/ja00159a042

Reference yield:

: 113161-31-2
3-benzyl-1,5-(dihydroxymethyl)-9-methylene-3-azabicyclo<3.3.1>nonane

: 124097-11-6
(+)-(1R,5S)-1-(acetoxymethyl)-3-benzyl-5-formyl-9-methylene-3-azabicyclo<3.3.1>nonane

Guidance literature:: Multi-step reaction with 3 steps

1: 1 percent / Candidia cylindracea lipase-type VII / benzene / 11 h / 28 °C

2: Celite, Candida cylindracea lipase-type VII / 2,2,4-trimethyl-pentane; H₂O / 48 h / 35 °C

3: 71 percent / COCl₂, DMSO, Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

With Candida cylindracea lipase-type VII; Candidia cylindracea lipase-type VII; Celite; dimethyl sulfoxide; triethylamine; In 2,2,4-trimethylpentane; dichloromethane; water; benzene;
DOI:10.1021/ja00159a042