(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-hydroxy-benzylamide

Base Information

• Chemical Name: (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-hydroxy-benzylamide
• CAS No.: 875012-89-8
• Molecular Formula: C₁₉H₂₁NO₂S
• Molecular Weight: 327.447

Synonyms:(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-hydroxy-benzylamide

Chemical Property of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-hydroxy-benzylamide

Chemical Property:

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Technology Process of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-hydroxy-benzylamide

There total 8 articles about (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-hydroxy-benzylamide 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:

(3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophene-1-carboxylic acid (875012-76-3) + 4-hydroxy-benzylamine hydrochloride (1004-23-5) → (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-hydroxy-benzylamide (875012-89-8)

Guidance literature:

(3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophene-1-carboxylic acid; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h;

4-hydroxy-benzylamine hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

Reference yield:

(3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophene-1-carboxylic acid (875012-76-3) + 4-aminomethylphenol (696-60-6) → (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-hydroxy-benzylamide (875012-89-8)

Guidance literature:

(3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophene-1-carboxylic acid; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

4-aminomethylphenol; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/jm4014373

Reference yield:

(+)-Δ3-carene (498-15-7,19079-29-9) → (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-hydroxy-benzylamide (875012-89-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: ozone / methanol / -65 °C

1.2: 2 h / 20 - 35 °C

2.1: thionyl chloride / 0.5 h / 0 °C

3.1: sodium methylate / methanol / 1 h / Reflux

4.1: triphenylphosphine; tetrachloromethane / tetrachloromethane / 65 °C

5.1: sodium ethanolate / ethanol / 0.08 h / 20 °C

5.2: 1 h / 20 °C

5.3: 1 h / 75 °C

6.1: lithium hydroxide; water / ethanol / 2 h / 75 °C

7.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C

7.2: 1 h / 20 °C

With tetrachloromethane; thionyl chloride; water; sodium methylate; sodium ethanolate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hydroxide; In methanol; tetrachloromethane; ethanol; N,N-dimethyl-formamide; 3.1: |Dieckmann Condensation;

DOI:10.1021/jm4014373

upstream raw materials:

(3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophene-1-carboxylic acid

4-hydroxy-benzylamine hydrochloride

(+)-Δ³-carene

(3¹R,3³S)-3²,3²-dimethyl-3(1,3)cyclopropyla-5-oxohexanoic acid

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