(1R,7aS)-1-Hydroxy-1-isopropenyl-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Base Information

Chemical Name:(1R,7aS)-1-Hydroxy-1-isopropenyl-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
CAS No.:160146-77-0
Molecular Formula:C₃₀H₄₂O₃
Molecular Weight:450.662
Hs Code.:

(1R,7aS)-1-Hydroxy-1-isopropenyl-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Synonyms:(1R,7aS)-1-Hydroxy-1-isopropenyl-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

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Chemical Property of (1R,7aS)-1-Hydroxy-1-isopropenyl-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

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Technology Process of (1R,7aS)-1-Hydroxy-1-isopropenyl-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

There total 14 articles about (1R,7aS)-1-Hydroxy-1-isopropenyl-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl 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: 56.0%

: 6386-71-6
isopropenyllithium

: 160146-75-8
(S)-7a-Methyl-1-oxo-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

: 160146-77-0
(1R,7aS)-1-Hydroxy-1-isopropenyl-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Guidance literature:: In diethyl ether; at -80 ℃;
DOI:10.1021/jo00099a002

Reference yield:

: 65253-04-5
(-)-8-phenylmenthol

: 160146-77-0
(1R,7aS)-1-Hydroxy-1-isopropenyl-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: DMAP / CH₂Cl₂ / 8 h / Heating

2: 56 percent / diethyl ether / -80 °C

With dmap; In diethyl ether; dichloromethane;
DOI:10.1021/jo00099a002

Reference yield:

: 765-69-5
2-Methylcyclopentane-1,3-dione

: 160146-77-0
(1R,7aS)-1-Hydroxy-1-isopropenyl-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 88 percent / Pd(OAc)2/PPh₃ / tetrahydrofuran / 6 h / Ambient temperature

2: 95 percent / TMSOTf / 10 h / -2 - 0 °C

3: 1.) BH₃*Me₂S, 2.) H₂O₂, 3 N NaOH / 1.) THF, 0 deg C to r.t., 4 h, 2.) r.t. 14 h

4: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

5: NaI, NaHCO₃ / acetone / 2.5 h / Heating

6: 70 percent / NaH / dimethylformamide / 13 h / Ambient temperature

7: 95 percent / Amberlyst-15 / acetone / 14 h / Ambient temperature

8: 80 percent / t-BuOK / tetrahydrofuran / 0.5 h / -80 °C

9: 56 percent / diethyl ether / -80 °C

With sodium hydroxide; dimethylsulfide borane complex; potassium tert-butylate; dihydrogen peroxide; sodium hydride; sodium hydrogencarbonate; triethylamine; sodium iodide; palladium diacetate; amberlyst-15; trimethylsilyl trifluoromethanesulfonate; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00099a002