7a-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one

Base Information

• Chemical Name: 7a-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one
• CAS No.: 481055-09-8
• Molecular Formula: C₂₃H₃₅NO₃Si
• Molecular Weight: 401.621
• Mol file: 481055-09-8.mol

Synonyms:7a-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one

Chemical Property of 7a-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7a-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one

There total 14 articles about 7a-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one 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: 67.0%

benzaldehyde dimethyl acetal (1125-88-8) + (R)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-5-hydroxymethyl-3-methyl-1,5-dihydro-pyrrol-2-one (481055-08-7) → 7a-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one (481055-09-8)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; Heating;

DOI:10.1016/S0040-4039(02)01459-4

Reference yield:

(E)-4-methyl-pent-2-en-1-ol (69143-05-1) → 7a-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one (481055-09-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 94 percent / Ti(i-PrO)4; (+)-DET; t-BuOOH / toluene; CH₂Cl₂ / -20 °C

2: 90 percent / DBU / CH₂Cl₂ / 0 °C

3: 70 percent / Et₂AlCl / CH₂Cl₂ / -10 °C

4: 98 percent / Et₃N / CH₂Cl₂ / 0 °C

5: 97 percent / aq. HCl / tetrahydrofuran / 20 °C

6: 73 percent / Et₃N / CH₂Cl₂ / 0 °C

7: 72 percent / CsOH*H₂O / dimethylformamide

8: 49 percent / KHMDS / toluene; diethyl ether

9: 85 percent / TPAP; NMO / acetonitrile

10: sodium chlorite; aq. NaH₂PO₄ / 2-methyl-propan-2-ol

11: NaBH₄ / methanol

12: 87 percent / TBAF / tetrahydrofuran

13: 67 percent / TsOH / toluene / Heating

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; cesium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; diethylaluminium chloride; potassium hexamethylsilazane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 1: Sharpless epoxidation;

DOI:10.1016/S0040-4039(02)01459-4

Reference yield:

ethyl-4-methyl-2-(E)-penteneoate (15790-86-0) → 7a-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one (481055-09-8)

Guidance literature:

Multi-step reaction with 14 steps

1: 62 percent / DIBAL-H / tetrahydrofuran / -78 °C

2: 94 percent / Ti(i-PrO)4; (+)-DET; t-BuOOH / toluene; CH₂Cl₂ / -20 °C

3: 90 percent / DBU / CH₂Cl₂ / 0 °C

4: 70 percent / Et₂AlCl / CH₂Cl₂ / -10 °C

5: 98 percent / Et₃N / CH₂Cl₂ / 0 °C

6: 97 percent / aq. HCl / tetrahydrofuran / 20 °C

7: 73 percent / Et₃N / CH₂Cl₂ / 0 °C

8: 72 percent / CsOH*H₂O / dimethylformamide

9: 49 percent / KHMDS / toluene; diethyl ether

10: 85 percent / TPAP; NMO / acetonitrile

11: sodium chlorite; aq. NaH₂PO₄ / 2-methyl-propan-2-ol

12: NaBH₄ / methanol

13: 87 percent / TBAF / tetrahydrofuran

14: 67 percent / TsOH / toluene / Heating

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; cesium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; diethylaluminium chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 2: Sharpless epoxidation;

DOI:10.1016/S0040-4039(02)01459-4

upstream raw materials:

benzaldehyde dimethyl acetal

(R)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-5-hydroxymethyl-3-methyl-1,5-dihydro-pyrrol-2-one

(E)-4-methyl-pent-2-en-1-ol

ethyl-4-methyl-2-(E)-penteneoate

Downstream raw materials:

(3S,7aR)-7a-((S)-1-Hydroxy-2-methyl-propyl)-6-methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one