(3R,3aR,4S,7R,7aS)-3-Benzyloxymethyl-7-bromo-7a-methyl-octahydro-inden-4-ol

Base Information

• Chemical Name: (3R,3aR,4S,7R,7aS)-3-Benzyloxymethyl-7-bromo-7a-methyl-octahydro-inden-4-ol
• CAS No.: 115333-78-3
• Molecular Formula: C₁₈H₂₅BrO₂
• Molecular Weight: 353.299
• Mol file: 115333-78-3.mol

Synonyms:(3R,3aR,4S,7R,7aS)-3-Benzyloxymethyl-7-bromo-7a-methyl-octahydro-inden-4-ol

Chemical Property of (3R,3aR,4S,7R,7aS)-3-Benzyloxymethyl-7-bromo-7a-methyl-octahydro-inden-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aR,4S,7R,7aS)-3-Benzyloxymethyl-7-bromo-7a-methyl-octahydro-inden-4-ol

There total 14 articles about (3R,3aR,4S,7R,7aS)-3-Benzyloxymethyl-7-bromo-7a-methyl-octahydro-inden-4-ol 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:

(+/-)-1,4,5,8,9,10-trans-hexahydronaphthalene-1,4-dione (2906-93-6,3198-51-4,6102-42-7,36159-09-8,54963-84-7,84275-37-6) → (3R,3aR,4S,7R,7aS)-3-Benzyloxymethyl-7-bromo-7a-methyl-octahydro-inden-4-ol (115333-78-3)

Guidance literature:

Multi-step reaction with 14 steps

1: LiAlH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

2: DMAP / pyridine

3: 1) O₃, Zn; 2) p-TsOH / 1) CH₂Cl₂, -78 deg C, AcOH-H₂O; 2) C₆H₆, reflux, 40 min.

4: H₂ / 10percent Pd-C / ethanol / 0.5 h / Ambient temperature

5: 1) Jones reagent; 2) LiAlH₄ / 1) acetone, 0 deg C, 10 min; 2) THF, -20 deg C, 2 h

6: 1) EtOCH=CH₂, PPTS; 2) LiAlH₄ / 1) CH₂Cl₂, room temp, 0.5 h; 2) THF, 0 deg. C, 1 h

7: 1) KH; 2) 0.5 M HCl / 1) DMF, room temp, 20 min; 2) DMF, room temp, 1.5 h

8: PCC / CH₂Cl₂ / 1.5 h / Ambient temperature

10: NaBH₄ / methanol / 0.67 h / 0 deg C -to room temp

11: Et₃N / CH₂Cl₂ / 40 h / 0 °C

12: 63 percent / tetrabutylammonium bromide / toluene / 20 h / 95 - 97 °C

13: H₂ ,1M HCl / 10percent Pd-C / ethanol / 1 h / Ambient temperature

14: NaH / dimethylformamide / 0.67 h / -70 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; tetrabutylammomium bromide; hydrogen; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; toluene-4-sulfonic acid; ozone; triethylamine; ethyl vinyl ether; pyridinium chlorochromate; zinc; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)96491-8

Reference yield:

(1R,3aR,4S,7S,7aR)-1-Hydroxymethyl-octahydro-indene-4,7-diol → (3R,3aR,4S,7R,7aS)-3-Benzyloxymethyl-7-bromo-7a-methyl-octahydro-inden-4-ol (115333-78-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) KH; 2) 0.5 M HCl / 1) DMF, room temp, 20 min; 2) DMF, room temp, 1.5 h

2: PCC / CH₂Cl₂ / 1.5 h / Ambient temperature

4: NaBH₄ / methanol / 0.67 h / 0 deg C -to room temp

5: Et₃N / CH₂Cl₂ / 40 h / 0 °C

6: 63 percent / tetrabutylammonium bromide / toluene / 20 h / 95 - 97 °C

7: H₂ ,1M HCl / 10percent Pd-C / ethanol / 1 h / Ambient temperature

8: NaH / dimethylformamide / 0.67 h / -70 °C

With hydrogenchloride; sodium tetrahydroborate; tetrabutylammomium bromide; hydrogen; potassium hydride; sodium hydride; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)96491-8

Reference yield:

(1R,4R,4aS,8aS)-1,2,3,4,4a,5,8,8a-Octahydro-naphthalene-1,4-diol (2906-96-9,2906-97-0,2907-00-8,3198-50-3,35043-96-0,51921-13-2,63950-09-4,63950-10-7,63950-11-8,79814-59-8,84173-22-8,84275-38-7,115404-51-8) → (3R,3aR,4S,7R,7aS)-3-Benzyloxymethyl-7-bromo-7a-methyl-octahydro-inden-4-ol (115333-78-3)

Guidance literature:

Multi-step reaction with 13 steps

1: DMAP / pyridine

2: 1) O₃, Zn; 2) p-TsOH / 1) CH₂Cl₂, -78 deg C, AcOH-H₂O; 2) C₆H₆, reflux, 40 min.

3: H₂ / 10percent Pd-C / ethanol / 0.5 h / Ambient temperature

4: 1) Jones reagent; 2) LiAlH₄ / 1) acetone, 0 deg C, 10 min; 2) THF, -20 deg C, 2 h

5: 1) EtOCH=CH₂, PPTS; 2) LiAlH₄ / 1) CH₂Cl₂, room temp, 0.5 h; 2) THF, 0 deg. C, 1 h

6: 1) KH; 2) 0.5 M HCl / 1) DMF, room temp, 20 min; 2) DMF, room temp, 1.5 h

7: PCC / CH₂Cl₂ / 1.5 h / Ambient temperature

9: NaBH₄ / methanol / 0.67 h / 0 deg C -to room temp

10: Et₃N / CH₂Cl₂ / 40 h / 0 °C

11: 63 percent / tetrabutylammonium bromide / toluene / 20 h / 95 - 97 °C

12: H₂ ,1M HCl / 10percent Pd-C / ethanol / 1 h / Ambient temperature

13: NaH / dimethylformamide / 0.67 h / -70 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; tetrabutylammomium bromide; hydrogen; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; toluene-4-sulfonic acid; ozone; triethylamine; ethyl vinyl ether; pyridinium chlorochromate; zinc; palladium on activated charcoal; In pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)96491-8

upstream raw materials:

benzyl bromide

(3R,3aR,4S,7R,7aS)-7-Bromo-3-hydroxymethyl-7a-methyl-octahydro-inden-4-ol

(+/-)-1,4,5,8,9,10-trans-hexahydronaphthalene-1,4-dione

(1R,4R,4aS,8aS)-1,2,3,4,4a,5,8,8a-Octahydro-naphthalene-1,4-diol

Downstream raw materials:

(3R,3aR,7R,7aS)-3-Benzyloxymethyl-7-bromo-7a-methyl-octahydro-inden-4-one

(+/-)-oppositol

(3S,3aR,4S,7aS)-3-Benzyloxymethyl-4,7a-dimethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-ol

(3R,3aS,4R,7R,7aS)-3-Benzyloxymethyl-7-bromo-4,7a-dimethyl-octahydro-inden-4-ol