methyl (1R*,2S*,3R*,5R*,8S*,9R*)-2,5,9-trimethyl-3-phenylselenyl-4-oxotricyclo<6.3.0.0^1,5>undecane-3-carboxylate

Base Information

• Chemical Name: methyl (1R*,2S*,3R*,5R*,8S*,9R*)-2,5,9-trimethyl-3-phenylselenyl-4-oxotricyclo<6.3.0.0^1,5>undecane-3-carboxylate
• CAS No.: 131615-18-4
• Molecular Formula: C₂₂H₂₈O₃Se
• Molecular Weight: 419.423
• Mol file: 131615-18-4.mol

Synonyms:

Chemical Property of methyl (1R*,2S*,3R*,5R*,8S*,9R*)-2,5,9-trimethyl-3-phenylselenyl-4-oxotricyclo<6.3.0.0^1,5>undecane-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1R*,2S*,3R*,5R*,8S*,9R*)-2,5,9-trimethyl-3-phenylselenyl-4-oxotricyclo<6.3.0.0^1,5>undecane-3-carboxylate

There total 29 articles about methyl (1R*,2S*,3R*,5R*,8S*,9R*)-2,5,9-trimethyl-3-phenylselenyl-4-oxotricyclo<6.3.0.0^1,5>undecane-3-carboxylate 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:

(1R*,5S*,8S*)-8-hydroxy-5-methylbicyclo<3.3.0>octan-2-one (110366-72-8,110366-73-9,131615-14-0,142619-48-5) → methyl (1R*,2S*,3R*,5R*,8S*,9R*)-2,5,9-trimethyl-3-phenylselenyl-4-oxotricyclo<6.3.0.01,5>undecane-3-carboxylate (131556-26-8,131615-18-4)

Guidance literature:

Multi-step reaction with 14 steps

1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 2) hexamethylphosphoric triamide (HMPT) / THF, Et₂O, 1) 1.1) -78 deg C, 1.5 h, 1.2) -48 deg C, 2.5 h, 2) 2.1) -48 deg C, to RT, 1.5 h, 2.2) RT, 45 min

4: 1) BH₃, 2) 30percent aq. H₂O₂, 3N NaOH / 1) THF, RT, 2 h , 2) THF, MeOH, reflux, 1,5 h

5: 1) oxalyl chloride, 2) Et₃N / DMSO, CH₂Cl₂, 1) -78 deg C, 1 h, 2) 0 deg C, 1 h

6: 85 percent / Et₂O*BF₃ / CH₂Cl₂ / 1 h / 0 °C

7: 74 percent / Raney nickel (W-4) / acetone / 1.5 h / Ambient temperature

8: 1) LDA / THF, 1) -78 deg C, 1 h, 2) RT, 1 h

9: 88 percent / Pd(OAc)2 / acetonitrile / 3.8 h / Ambient temperature

10: 96 percent / diethyl ether; tetrahydrofuran / 1.5 h / -78 °C

11: 88 percent / PCC / CH₂Cl₂ / 1 h / Ambient temperature

12: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h / Ambient temperature

13: 1) LDA, 2) HMPT / THF, 1) -78 deg C, 50 min., 2) -78 deg C, 90 min.

14: 1) LDA / THF, 1) -78 deg C, 40 min., 2) -78 deg C, 25 min.

With N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium hydroxide; oxalyl dichloride; Raney nickel (W-4); boron trifluoride diethyl etherate; borane; hydrogen; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; acetonitrile;

DOI:10.1055/s-1992-34160

Reference yield:

(RS)-5-methylbicyclo<3.3.0>oct-1(8)-en-2-one (131572-31-1) → (1S,2S,3aR,5aS,6R,8aR)-1,3a,6-Trimethyl-3-oxo-2-phenylselanyl-decahydro-cyclopenta[c]pentalene-2-carboxylic acid methyl ester (131556-26-8,131615-18-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 2) hexamethylphosphoric triamide (HMPT) / THF, Et₂O, 1) 1.1) -78 deg C, 1.5 h, 1.2) -48 deg C, 2.5 h, 2) 2.1) -48 deg C, to RT, 1.5 h, 2.2) RT, 45 min

2: 1) BH₃, 2) 30percent aq. H₂O₂, 3N NaOH / 1) THF, RT, 2 h , 2) THF, MeOH, reflux, 1,5 h

3: 1) oxalyl chloride, 2) Et₃N / DMSO, CH₂Cl₂, 1) -78 deg C, 1 h, 2) 0 deg C, 1 h

4: 85 percent / Et₂O*BF₃ / CH₂Cl₂ / 1 h / 0 °C

5: 74 percent / Raney nickel (W-4) / acetone / 1.5 h / Ambient temperature

6: 1) LDA / THF, 1) -78 deg C, 1 h, 2) RT, 1 h

7: 88 percent / Pd(OAc)2 / acetonitrile / 3.8 h / Ambient temperature

8: 96 percent / diethyl ether; tetrahydrofuran / 1.5 h / -78 °C

9: 88 percent / PCC / CH₂Cl₂ / 1 h / Ambient temperature

10: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h / Ambient temperature

11: 1) LDA, 2) HMPT / THF, 1) -78 deg C, 50 min., 2) -78 deg C, 90 min.

12: 1) LDA / THF, 1) -78 deg C, 40 min., 2) -78 deg C, 25 min.

With N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium hydroxide; oxalyl dichloride; Raney nickel (W-4); boron trifluoride diethyl etherate; borane; hydrogen; dihydrogen peroxide; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; acetonitrile;

DOI:10.1055/s-1992-34160

Reference yield:

(RS)-5-methylbicyclo<3.3.0>oct-1(8)-en-2-one (131572-31-1) → methyl (1R*,2S*,3R*,5R*,8S*,9R*)-2,5,9-trimethyl-3-phenylselenyl-4-oxotricyclo<6.3.0.01,5>undecane-3-carboxylate (131556-26-8,131615-18-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 2) hexamethylphosphoric triamide (HMPT) / THF, Et₂O, 1) 1.1) -78 deg C, 1.5 h, 1.2) -48 deg C, 2.5 h, 2) 2.1) -48 deg C, to RT, 1.5 h, 2.2) RT, 45 min

2: 1) BH₃, 2) 30percent aq. H₂O₂, 3N NaOH / 1) THF, RT, 2 h , 2) THF, MeOH, reflux, 1,5 h

3: 1) oxalyl chloride, 2) Et₃N / DMSO, CH₂Cl₂, 1) -78 deg C, 1 h, 2) 0 deg C, 1 h

4: 85 percent / Et₂O*BF₃ / CH₂Cl₂ / 1 h / 0 °C

5: 74 percent / Raney nickel (W-4) / acetone / 1.5 h / Ambient temperature

6: 1) LDA / THF, 1) -78 deg C, 1 h, 2) RT, 1 h

7: 88 percent / Pd(OAc)2 / acetonitrile / 3.8 h / Ambient temperature

8: 96 percent / diethyl ether; tetrahydrofuran / 1.5 h / -78 °C

9: 88 percent / PCC / CH₂Cl₂ / 1 h / Ambient temperature

10: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h / Ambient temperature

11: 1) LDA, 2) HMPT / THF, 1) -78 deg C, 50 min., 2) -78 deg C, 90 min.

12: 1) LDA / THF, 1) -78 deg C, 40 min., 2) -78 deg C, 25 min.

With N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium hydroxide; oxalyl dichloride; Raney nickel (W-4); boron trifluoride diethyl etherate; borane; hydrogen; dihydrogen peroxide; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; acetonitrile;

DOI:10.1055/s-1992-34160

upstream raw materials:

(RS)-5-methylbicyclo<3.3.0>oct-1(8)-en-2-one

(1R*,5S*,8S*)-8-hydroxy-5-methylbicyclo<3.3.0>octan-2-one

(1R*,5R*,8R*,9S*)-5,9-dimethyltricyclo<6.3.0.0^1,5>undecan-2-one

(1R*,5R*,8R*,9S*)-5,9-dimethyltricyclo<6.3.0.0^1,5>undec-3-en-2-one