(-)-(1R,5S,7S)-3-[(1R)-2-hydroxy-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-en-4-one

Base Information

• Chemical Name: (-)-(1R,5S,7S)-3-[(1R)-2-hydroxy-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-en-4-one
• CAS No.: 77704-39-3
• Molecular Formula: C₁₈H₂₁NO₃
• Molecular Weight: 299.37

Synonyms:(-)-(1R,5S,7S)-3-[(1R)-2-hydroxy-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-en-4-one

Chemical Property of (-)-(1R,5S,7S)-3-[(1R)-2-hydroxy-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-en-4-one

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Technology Process of (-)-(1R,5S,7S)-3-[(1R)-2-hydroxy-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-en-4-one

There total 17 articles about (-)-(1R,5S,7S)-3-[(1R)-2-hydroxy-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-en-4-one 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: 69.0%

(-)-(R)-N-<(Furan-2-yl)methyl>-N-(2-hyydroxy-1-phenylethyl)-3-methylbut-2-enamid (77704-70-2) → (-)-(1R,5S,7S)-3-[(1R)-2-hydroxy-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.01,5]dec-8-en-4-one (77704-39-3)

Guidance literature:

(-)-(R)-N-<(Furan-2-yl)methyl>-N-(2-hyydroxy-1-phenylethyl)-3-methylbut-2-enamid; With butyl magnesium bromide; In diethyl ether; at -60 ℃; for 0.75h;

In toluene; for 16h; Heating;

DOI:10.1039/b201987f

Reference yield:

(-)-(R)-2<<(Furan-2-yl)methyl>amino>-2-phenylethanol (132168-60-6) → (-)-(1R,5S,7S)-3-[(1R)-2-hydroxy-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.01,5]dec-8-en-4-one (77704-39-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / tetrahydrofuran / 2 h

2.1: pyridine / tetrahydrofuran / 16 h

3.1: 139 g / aq. HCl / tetrahydrofuran

4.1: n-BuMgCl / diethyl ether / 0.75 h / -60 °C

4.2: 69 percent / toluene / 16 h / Heating

With pyridine; hydrogenchloride; butyl magnesium bromide; In tetrahydrofuran; diethyl ether; 4.2: intramolecular Diels-Alder reaction;

DOI:10.1039/b201987f

Reference yield:

D-2-phenylglycinol (56613-80-0) → (-)-(1R,5S,7S)-3-[(1R)-2-hydroxy-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.01,5]dec-8-en-4-one (77704-39-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: toluene / Heating

2.1: NaBH₄ / propan-2-ol

3.1: pyridine / tetrahydrofuran

5.1: aq. HCl

6.1: n-BuMgCl / diethyl ether / -60 °C

6.2: toluene / 16 h / Heating

With pyridine; hydrogenchloride; sodium tetrahydroborate; butyl magnesium bromide; In tetrahydrofuran; diethyl ether; isopropyl alcohol; toluene; 1.1: Condensation / 2.1: Reduction / 3.1: Etherification / 4.1: Acylation / 5.1: Hydrolysis / 6.1: Metallation / 6.2: Cyclization;

DOI:10.1039/b003757p

upstream raw materials:

(-)-(R)-N-<(Furan-2-yl)methyl>-N-(2-hyydroxy-1-phenylethyl)-3-methylbut-2-enamid

furfural

3,3-Dimethylacryloyl chloride

D-2-phenylglycinol

Downstream raw materials:

(1R,5S,7S)-3-[(1R)-2-chloro-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-en-4-one

(+)-(1R,2S,4R,5S)-1-(tert-butyldiphenylsilyloxy)-1-formyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

(+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-1-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

(+)-(1R,2S,4R,5S)-1-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

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