(1S,2S,6R,7R)-4-(1-Methoxymethoxy-2-phenyl-ethyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene

Base Information

• Chemical Name: (1S,2S,6R,7R)-4-(1-Methoxymethoxy-2-phenyl-ethyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene
• CAS No.: 89426-78-8
• Molecular Formula: C₂₁H₂₉NO₃
• Molecular Weight: 343.466

Synonyms:(1S,2S,6R,7R)-4-(1-Methoxymethoxy-2-phenyl-ethyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene

Chemical Property of (1S,2S,6R,7R)-4-(1-Methoxymethoxy-2-phenyl-ethyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene

Chemical Property:

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Technology Process of (1S,2S,6R,7R)-4-(1-Methoxymethoxy-2-phenyl-ethyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene

There total 5 articles about (1S,2S,6R,7R)-4-(1-Methoxymethoxy-2-phenyl-ethyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 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:

(1S)-camphor (464-48-2,68546-28-1) → (1S,2S,6R,7R)-4-(1-Methoxymethoxy-2-phenyl-ethyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-ene (89426-78-8)

Guidance literature:

Multi-step reaction with 5 steps

1: isoamyl nitrite

2: NaBH₄ / ethanol

3: H₂ / PtO₂ / xylene

4: 51 percent / ZnCl₂ / 50 h / 100 °C

5: 1.) n-BuLi in hexane / 1.) ether, -78 deg C, THF 2.) alkyl halyd adding 45 mn, then 2h at -78 deg C

With sodium tetrahydroborate; n-butyllithium; hydrogen; isopentyl nitrite; platinum(IV) oxide; zinc(II) chloride; In ethanol; xylene;

DOI:10.1016/S0040-4039(01)91142-6

Reference yield:

3-(hydroxyimino)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (251645-83-7) → (1S,2S,6R,7R)-4-(1-Methoxymethoxy-2-phenyl-ethyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-ene (89426-78-8)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄ / ethanol

2: H₂ / PtO₂ / xylene

3: 51 percent / ZnCl₂ / 50 h / 100 °C

4: 1.) n-BuLi in hexane / 1.) ether, -78 deg C, THF 2.) alkyl halyd adding 45 mn, then 2h at -78 deg C

With sodium tetrahydroborate; n-butyllithium; hydrogen; platinum(IV) oxide; zinc(II) chloride; In ethanol; xylene;

DOI:10.1016/S0040-4039(01)91142-6

Reference yield:

(1R,3S,4S)-3-Hydroxy-4,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one oxime (25050-52-6,29900-92-3,32231-88-2,32231-96-2,32231-97-3,32231-98-4,72656-83-8,131897-85-3,131897-86-4) → (1S,2S,6R,7R)-4-(1-Methoxymethoxy-2-phenyl-ethyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-ene (89426-78-8)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / PtO₂ / xylene

2: 51 percent / ZnCl₂ / 50 h / 100 °C

3: 1.) n-BuLi in hexane / 1.) ether, -78 deg C, THF 2.) alkyl halyd adding 45 mn, then 2h at -78 deg C

With n-butyllithium; hydrogen; platinum(IV) oxide; zinc(II) chloride; In xylene;

DOI:10.1016/S0040-4039(01)91142-6

upstream raw materials:

benzyl bromide

(1S,2S,6R,7R)-4-Methoxymethoxymethyl-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene

(1S)-camphor

3-(hydroxyimino)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Downstream raw materials:

L-3-phenyllactic acid

D-phenyllactic acid

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-methoxycarbonyl-2-phenyl-ethyl ester

(S)-methyl 2-hydroxy-3-phenylpropanoate

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