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

Base Information

• Chemical Name: N-<(2R,3R)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane
• CAS No.: 147253-91-6
• Molecular Formula: C₂₀H₂₅NO₃S
• Molecular Weight: 359.489

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

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

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

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

(+)-1-isocyanato-7,7-dimethylbicyclo[2.2.1]heptan-2-one (137329-22-7) → N-<(2R,3R)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.01,5>decane (147253-91-6)

Guidance literature:

Multi-step reaction with 4 steps

1: CeCl₃*7H₂O, 2.) NaBH₄ / 1.) MeOH, 0 deg C, 10 min, 2.) MeOH, -50 deg C to -36 deg C, 2 h

2: 100 percent / Et₃N / tetrahydrofuran / 15 h / Heating

3: 1.) NaH / 1.) THF, 0 deg C, 25 min, 2.) THF, 0 deg C, 30 min

4: 1.) TiCl₄, 2.) diisopropylethylamine

With sodium tetrahydroborate; cerium(III) chloride; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/ja00060a010

Reference yield:

(1S,2R,4R)-1-amino-2-exo-hydroxy-7,7-dimethyl-bicyclo[2.2.1]heptane (147168-89-6,793645-97-3) → N-<(2R,3R)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.01,5>decane (147253-91-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Et₃N / tetrahydrofuran / 15 h / Heating

2: 1.) NaH / 1.) THF, 0 deg C, 25 min, 2.) THF, 0 deg C, 30 min

3: 1.) TiCl₄, 2.) diisopropylethylamine

With titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/ja00060a010

Reference yield:

(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.01,5>decane (147168-90-9) → N-<(2R,3R)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.01,5>decane (147253-91-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) THF, 0 deg C, 25 min, 2.) THF, 0 deg C, 30 min

2: 1.) TiCl₄, 2.) diisopropylethylamine

With titanium tetrachloride; sodium hydride; N-ethyl-N,N-diisopropylamine;

DOI:10.1021/ja00060a010

upstream raw materials:

(+)-1-isocyanato-7,7-dimethylbicyclo[2.2.1]heptan-2-one

(1S,2R,4R)-1-amino-2-exo-hydroxy-7,7-dimethyl-bicyclo[2.2.1]heptane

(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane

Downstream raw materials:

(2R,3R)-3-hydroxy-2-methyl-3-phenylpropionic acid benzyl ester

methyl (2R,3R)-3-hydroxy-2-methyl-3-phenylpropanoate

(2R,3R)-(+)-3-hydroxy-2-methyl-3-phenylpropanoic acid

(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane

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