(1R,5R,9R)-1-Formyl-5-methyl-9-[2-(6-oxo-cyclohex-1-enyl)-ethyl]-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

Base Information

Chemical Name:(1R,5R,9R)-1-Formyl-5-methyl-9-[2-(6-oxo-cyclohex-1-enyl)-ethyl]-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester
CAS No.:124022-43-1
Molecular Formula:C₂₀H₂₉NO₄
Molecular Weight:347.455
Hs Code.:

Synonyms:(1R,5R,9R)-1-Formyl-5-methyl-9-[2-(6-oxo-cyclohex-1-enyl)-ethyl]-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

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Chemical Property of (1R,5R,9R)-1-Formyl-5-methyl-9-[2-(6-oxo-cyclohex-1-enyl)-ethyl]-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

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Technology Process of (1R,5R,9R)-1-Formyl-5-methyl-9-[2-(6-oxo-cyclohex-1-enyl)-ethyl]-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

There total 15 articles about (1R,5R,9R)-1-Formyl-5-methyl-9-[2-(6-oxo-cyclohex-1-enyl)-ethyl]-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester 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:

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

: 124022-43-1
(1R,5R,9R)-1-Formyl-5-methyl-9-[2-(6-oxo-cyclohex-1-enyl)-ethyl]-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 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

4: 1.) H₂NNH₂*H₂O, 2.) NaOH / 1.) triethylane glycol, 120 deg C, 2 h, 2.) 170 deg C, 18 h

5: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / Ambient temperature

6: 1.) BF₃*Et₂O, NaBH₄, 2.) Me₃NO / 1.) diglyme, -23 deg C, 18 h, 2.) 120 deg C, 11 h

7: HCO₂NH₄ / 10percent Pd/C / methanol / 0.17 h / Heating

8: 44percent aq. K₂CO₃ / benzene / 16 h / Ambient temperature

9: 86 percent / COCl₂, DMSO, Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

10: 1.) n-BuLi / 1.) THF, hexane, RT, 30 min, 2.) RT, 3 h

11: 100 percent / concd HCl / methanol / 12 h / 55 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; trimethylamine-N-oxide; Candida cylindracea lipase-type VII; Candidia cylindracea lipase-type VII; Celite; boron trifluoride diethyl etherate; ammonium formate; potassium carbonate; hydrazine hydrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; 2,2,4-trimethylpentane; dichloromethane; water; benzene;
DOI:10.1021/ja00159a042

Reference yield:

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

: 124022-43-1
(1R,5R,9R)-1-Formyl-5-methyl-9-[2-(6-oxo-cyclohex-1-enyl)-ethyl]-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 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

5: 1.) H₂NNH₂*H₂O, 2.) NaOH / 1.) triethylane glycol, 120 deg C, 2 h, 2.) 170 deg C, 18 h

6: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / Ambient temperature

7: 1.) BF₃*Et₂O, NaBH₄, 2.) Me₃NO / 1.) diglyme, -23 deg C, 18 h, 2.) 120 deg C, 11 h

8: HCO₂NH₄ / 10percent Pd/C / methanol / 0.17 h / Heating

9: 44percent aq. K₂CO₃ / benzene / 16 h / Ambient temperature

10: 86 percent / COCl₂, DMSO, Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

11: 1.) n-BuLi / 1.) THF, hexane, RT, 30 min, 2.) RT, 3 h

12: 100 percent / concd HCl / methanol / 12 h / 55 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; trimethylamine-N-oxide; Candida cylindracea lipase-type VII; Candidia cylindracea lipase-type VII; Celite; boron trifluoride diethyl etherate; ammonium formate; potassium carbonate; hydrazine hydrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; water; benzene;
DOI:10.1021/ja00159a042

Reference yield:

: 113161-21-0
dimethyl 3-benzyl-3-azabicyclo<3.3.1>nonan-9-one-1,5-dicarboxylate

: 124022-43-1
(1R,5R,9R)-1-Formyl-5-methyl-9-[2-(6-oxo-cyclohex-1-enyl)-ethyl]-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) KH, tert-pentyl alcohol / 1.) benzene, RT, 1 h, 2.) reflux, 1.5 h

2: 93 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

3: 1 percent / Candidia cylindracea lipase-type VII / benzene / 11 h / 28 °C

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

5: 71 percent / COCl₂, DMSO, Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

6: 1.) H₂NNH₂*H₂O, 2.) NaOH / 1.) triethylane glycol, 120 deg C, 2 h, 2.) 170 deg C, 18 h

7: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / Ambient temperature

8: 1.) BF₃*Et₂O, NaBH₄, 2.) Me₃NO / 1.) diglyme, -23 deg C, 18 h, 2.) 120 deg C, 11 h

9: HCO₂NH₄ / 10percent Pd/C / methanol / 0.17 h / Heating

10: 44percent aq. K₂CO₃ / benzene / 16 h / Ambient temperature

11: 86 percent / COCl₂, DMSO, Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

12: 1.) n-BuLi / 1.) THF, hexane, RT, 30 min, 2.) RT, 3 h

13: 100 percent / concd HCl / methanol / 12 h / 55 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; tert-Amyl alcohol; trimethylamine-N-oxide; Candida cylindracea lipase-type VII; Candidia cylindracea lipase-type VII; Celite; boron trifluoride diethyl etherate; ammonium formate; potassium hydride; potassium carbonate; hydrazine hydrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; water; benzene;
DOI:10.1021/ja00159a042