(+)-(1R,5R,9R)-3-benzyl-9-(hydroxymethyl)-1-<((methoxymethyl)oxy)methyl>-5-methyl-3-azabicyclo<3.3.1>nonane

Base Information

Chemical Name:(+)-(1R,5R,9R)-3-benzyl-9-(hydroxymethyl)-1-<((methoxymethyl)oxy)methyl>-5-methyl-3-azabicyclo<3.3.1>nonane
CAS No.:124097-13-8
Molecular Formula:C₂₀H₃₁NO₃
Molecular Weight:333.471
Hs Code.:

Synonyms:(+)-(1R,5R,9R)-3-benzyl-9-(hydroxymethyl)-1-<((methoxymethyl)oxy)methyl>-5-methyl-3-azabicyclo<3.3.1>nonane

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Chemical Property of (+)-(1R,5R,9R)-3-benzyl-9-(hydroxymethyl)-1-<((methoxymethyl)oxy)methyl>-5-methyl-3-azabicyclo<3.3.1>nonane

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Technology Process of (+)-(1R,5R,9R)-3-benzyl-9-(hydroxymethyl)-1-<((methoxymethyl)oxy)methyl>-5-methyl-3-azabicyclo<3.3.1>nonane

There total 8 articles about (+)-(1R,5R,9R)-3-benzyl-9-(hydroxymethyl)-1-<((methoxymethyl)oxy)methyl>-5-methyl-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:

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

: 124097-13-8
(+)-(1R,5R,9R)-3-benzyl-9-(hydroxymethyl)-1-<((methoxymethyl)oxy)methyl>-5-methyl-3-azabicyclo<3.3.1>nonane

Guidance literature:: Multi-step reaction with 6 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

With sodium hydroxide; sodium tetrahydroborate; trimethylamine-N-oxide; Candida cylindracea lipase-type VII; Candidia cylindracea lipase-type VII; Celite; boron trifluoride diethyl etherate; hydrazine hydrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In 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

: 124097-13-8
(+)-(1R,5R,9R)-3-benzyl-9-(hydroxymethyl)-1-<((methoxymethyl)oxy)methyl>-5-methyl-3-azabicyclo<3.3.1>nonane

Guidance literature:: Multi-step reaction with 7 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

With sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; trimethylamine-N-oxide; Candida cylindracea lipase-type VII; Candidia cylindracea lipase-type VII; Celite; boron trifluoride diethyl etherate; hydrazine hydrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 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

: 124097-13-8
(+)-(1R,5R,9R)-3-benzyl-9-(hydroxymethyl)-1-<((methoxymethyl)oxy)methyl>-5-methyl-3-azabicyclo<3.3.1>nonane

Guidance literature:: Multi-step reaction with 8 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

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