4-{(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-3-oxo-butyric acid tert-butyl ester

Base Information

• Chemical Name: 4-{(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-3-oxo-butyric acid tert-butyl ester
• CAS No.: 250595-72-3
• Molecular Formula: C₃₆H₅₃NO₄Si
• Molecular Weight: 591.907
• Mol file: 250595-72-3.mol

Synonyms:4-{(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-3-oxo-butyric acid tert-butyl ester

Chemical Property of 4-{(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-3-oxo-butyric acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-3-oxo-butyric acid tert-butyl ester

There total 15 articles about 4-{(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-3-oxo-butyric acid tert-butyl 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: 86.0%

acetic acid tert-butyl ester (540-88-5) + {(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-acetic acid methyl ester (250595-71-2) → 4-{(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-3-oxo-butyric acid tert-butyl ester (250595-72-3)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -50 - 20 ℃;

DOI:10.1016/S0040-4039(99)01170-3

Reference yield:

(2-oxocyclopent)acetic acid (104115-44-8,1460-38-4) → 4-{(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-3-oxo-butyric acid tert-butyl ester (250595-72-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 95 percent / toluene / Heating

2.1: 99 percent / TiCl₄ / CH₂Cl₂ / -78 - 20 °C

3.1: 92 percent / Na; NH₃ / tetrahydrofuran; ethanol / -78 °C

4.1: 96 percent / DMAP / tetrahydrofuran

5.1: LiHMDS / tetrahydrofuran / -40 °C

5.2: 90 percent / tetrahydrofuran / -78 - 0 °C

6.1: 89 percent / LiOH; H₂O / tetrahydrofuran

7.1: NEt₃ / tetrahydrofuran

8.1: NaBH₄ / methanol

9.1: 95 percent / NEt₃; DMAP / CH₂Cl₂

10.1: 9-BBN / tetrahydrofuran

10.2: AsPh₃; Cs₂CO₃; H₂O / [Pd(dppf)Cl₂] / dimethylformamide

11.1: TFA / CH₂Cl₂

12.1: K₂CO₃ / H₂O

13.1: 86 percent / LiHMDS / tetrahydrofuran / -50 - 20 °C

With dmap; lithium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; ammonia; water; sodium; titanium tetrachloride; potassium carbonate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; 1.1: Cyclization / 2.1: Ring cleavage / 3.1: Reduction / 4.1: Acylation / 5.1: Metallation / 5.2: Methylation / 6.1: Hydrolysis / 7.1: Acylation / 8.1: Reduction / 9.1: Etherification / 10.1: Addition / 10.2: Alkylation / 11.1: Deacylation / 12.1: Michael reaction / 13.1: Condensation;

DOI:10.1002/(SICI)1521-3773(19991203)38:23<3542::AID-ANIE3542>3.0.CO;2-I

Reference yield:

(3aR,6aS)-6a-Allyl-hexahydro-cyclopenta[b]pyrrol-2-one (250595-64-3) → 4-{(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-3-oxo-butyric acid tert-butyl ester (250595-72-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 96 percent / DMAP / tetrahydrofuran

2.1: LiHMDS / tetrahydrofuran / -40 °C

2.2: 90 percent / tetrahydrofuran / -78 - 0 °C

3.1: 89 percent / LiOH; H₂O / tetrahydrofuran

4.1: NEt₃ / tetrahydrofuran

5.1: NaBH₄ / methanol

6.1: 95 percent / NEt₃; DMAP / CH₂Cl₂

7.1: 9-BBN / tetrahydrofuran

7.2: AsPh₃; Cs₂CO₃; H₂O / [Pd(dppf)Cl₂] / dimethylformamide

8.1: TFA / CH₂Cl₂

9.1: K₂CO₃ / H₂O

10.1: 86 percent / LiHMDS / tetrahydrofuran / -50 - 20 °C

With dmap; lithium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; water; potassium carbonate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Acylation / 2.1: Metallation / 2.2: Methylation / 3.1: Hydrolysis / 4.1: Acylation / 5.1: Reduction / 6.1: Etherification / 7.1: Addition / 7.2: Alkylation / 8.1: Deacylation / 9.1: Michael reaction / 10.1: Condensation;

DOI:10.1002/(SICI)1521-3773(19991203)38:23<3542::AID-ANIE3542>3.0.CO;2-I

upstream raw materials:

acetic acid tert-butyl ester

{(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-acetic acid methyl ester

(2-oxocyclopent)acetic acid

(3R,5aR,8aS)-3-phenyl-hexahydro-1-oxa-3a-aza-cyclopenta[c]pentalen-4-one

Downstream raw materials:

C₃₇H₅₃NO₄Si

C₃₇H₅₃NO₃Si