N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo<5.2.1.0^2,6>decane

Base Information

• Chemical Name: N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo<5.2.1.0^2,6>decane
• CAS No.: 131793-58-3
• Molecular Formula: C₂₁H₂₇NO₄
• Molecular Weight: 357.45

Synonyms:N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo<5.2.1.0^2,6>decane

Chemical Property of N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo<5.2.1.0^2,6>decane

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Technology Process of N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo<5.2.1.0^2,6>decane

There total 5 articles about N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo<5.2.1.0^2,6>decane 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:

(R)-camphorquinone (10334-26-6) → N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo<5.2.1.02,6>decane (131793-58-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / H₂NOH*HCl, sodium acetate / H₂O; ethanol / 0.17 h / Heating

2: 93 percent / NaBH₄ / ethanol / 35 h / 25 °C

3: 85 percent / H₂ / PtO₂ / xylene / 9 h / 25 °C / 2584 Torr

4: 88 percent / toluene / 0.67 h / 0 °C

5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) -70 deg C, 1 h

With sodium tetrahydroborate; n-butyllithium; hydroxylamine hydrochloride; hydrogen; sodium acetate; platinum(IV) oxide; In ethanol; water; toluene; xylene;

DOI:10.1021/ja00004a034

Reference yield:

(1R,2S,4S)-2-exo-hydroxy-3-(hydroxyimino)-1,7,7-trimethylbicyclo<2.2.1>heptane (162425-97-0) → N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo<5.2.1.02,6>decane (131793-58-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / H₂ / PtO₂ / xylene / 9 h / 25 °C / 2584 Torr

2: 88 percent / toluene / 0.67 h / 0 °C

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) -70 deg C, 1 h

With n-butyllithium; hydrogen; platinum(IV) oxide; In toluene; xylene;

DOI:10.1021/ja00004a034

Reference yield:

(1R,4S)-3-hydroxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (663-17-2,5338-41-0,13854-86-9,13854-87-0,22472-58-8,31571-14-9,103833-77-8) → N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo<5.2.1.02,6>decane (131793-58-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / NaBH₄ / ethanol / 35 h / 25 °C

2: 85 percent / H₂ / PtO₂ / xylene / 9 h / 25 °C / 2584 Torr

3: 88 percent / toluene / 0.67 h / 0 °C

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) -70 deg C, 1 h

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

DOI:10.1021/ja00004a034

upstream raw materials:

N-propionyl-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo<5.2.1.0^2,6>decane

benzaldehyde

(R)-camphorquinone

(1R,2S,4S)-2-exo-hydroxy-3-(hydroxyimino)-1,7,7-trimethylbicyclo<2.2.1>heptane

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