Benzoic acid (S)-2-((1R,7aR)-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propyl ester

Base Information

• Chemical Name: Benzoic acid (S)-2-((1R,7aR)-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propyl ester
• CAS No.: 64190-55-2
• Molecular Formula: C₂₀H₂₆O₂
• Molecular Weight: 298.425
• Mol file: 64190-55-2.mol

Synonyms:Benzoic acid (S)-2-((1R,7aR)-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propyl ester

Chemical Property of Benzoic acid (S)-2-((1R,7aR)-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (S)-2-((1R,7aR)-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propyl ester

There total 1 articles about Benzoic acid (S)-2-((1R,7aR)-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propyl ester 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:

(S)-2-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyloctahydro-1H-inden-1-yl)propyl benzoate → Benzoic acid (S)-2-((1R,7aR)-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propyl ester (64190-55-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 18h; Heating;

DOI:10.1021/jo0608725

Reference yield:

Benzoic acid (S)-2-((1R,7aR)-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propyl ester (64190-55-2) → (3S,5S,9R,10R,13R,17R)-3-(Dimethyl-phenyl-silanyl)-17-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4,4,10,13-tetramethyl-1,2,3,4,5,6,9,10,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-7-one

Guidance literature:

Multi-step reaction with 19 steps

1: 0.062 g / NaOH / methanol; H₂O / 18 h / 20 °C

2: 74 percent / tetrabutylammonium iodide; NaH / tetrahydrofuran / 18 h / Heating

3: 0.308 g / m-chloroperoxybenzoic acid / CH₂Cl₂ / 2 h / -15 °C

4: 0.192 g / KOH / dimethylsulfoxide; H₂O / 18 h / 140 °C

5: triethylamine / tetrahydrofuran / 4 h / 20 °C

6: 4-(dimethylamino)pyridine; N,N-diisopropylethylamine / CH₂Cl₂ / 72 h / 20 °C

7: 1.17 g / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

8: 98 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / 20 °C

9: 81 percent / LHMDS / tetrahydrofuran / 2 h / -45 °C

10: 87 percent / triethylamine; PdCl₂(PPh₃)2 / dimethylformamide / 18 h / 55 °C / 18100.2 Torr

11: 79 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

12: 98 percent / triethylamine; oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

13: 94 percent / LHMDS / tetrahydrofuran / 0.5 h / -78 °C

14: 79 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

15: 55 percent / Cs₂CO₃ / acetonitrile / 6 h / 20 °C

16: 90 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 2 h / Heating

17: 60 percent / Me₄NBH(OAc)3 / acetonitrile / 6 h / -20 °C

18: 61 percent / NaH / tetrahydrofuran / 6 h / 60 °C

19: 50 percent / (Me₃Si)3SiH; 2,2'-azobisisobutyronitrile / toluene / 2 h / Heating

With morpholine; dmap; bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; sodium hydroxide; tetrapropylammonium perruthennate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 12: Swern oxidation;

DOI:10.1021/jo0608725

Reference yield:

Benzoic acid (S)-2-((1R,7aR)-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propyl ester (64190-55-2) → (3S,5S,9S,10R,13R,17R)-3-(Dimethyl-phenyl-silanyl)-17-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4,4,13-trimethyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carbaldehyde (908255-79-8)

Guidance literature:

Multi-step reaction with 16 steps

1: 0.062 g / NaOH / methanol; H₂O / 18 h / 20 °C

2: 74 percent / tetrabutylammonium iodide; NaH / tetrahydrofuran / 18 h / Heating

3: 0.308 g / m-chloroperoxybenzoic acid / CH₂Cl₂ / 2 h / -15 °C

4: 0.192 g / KOH / dimethylsulfoxide; H₂O / 18 h / 140 °C

5: triethylamine / tetrahydrofuran / 4 h / 20 °C

6: 4-(dimethylamino)pyridine; N,N-diisopropylethylamine / CH₂Cl₂ / 72 h / 20 °C

7: 1.17 g / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

8: 98 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / 20 °C

9: 81 percent / LHMDS / tetrahydrofuran / 2 h / -45 °C

10: 87 percent / triethylamine; PdCl₂(PPh₃)2 / dimethylformamide / 18 h / 55 °C / 18100.2 Torr

11: 79 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

12: 98 percent / triethylamine; oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

13: 94 percent / LHMDS / tetrahydrofuran / 0.5 h / -78 °C

14: 79 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

15: 55 percent / Cs₂CO₃ / acetonitrile / 6 h / 20 °C

16: 90 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 2 h / Heating

With morpholine; dmap; bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; sodium hydroxide; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 12: Swern oxidation;

DOI:10.1021/jo0608725

Downstream raw materials:

(3R,3aR)-3-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methyl-2,3,3a,4,5,6-hexahydro-1H-indene

(1R,3aR,4R,7aR)-1-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-7a-methyl-octahydro-indene-3a,4-diol

(1R,3aR,7aR)-1-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carbaldehyde

(1R,3aR,7aR)-1-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-octahydro-inden-4-one