{(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

Base Information

• Chemical Name: {(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
• CAS No.: 250595-71-2
• Molecular Formula: C₃₁H₄₅NO₃Si
• Molecular Weight: 507.789

Synonyms:{(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

Chemical Property of {(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

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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MSDS Files:

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Technology Process of {(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

There total 13 articles about {(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 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:

(2-oxocyclopent)acetic acid (104115-44-8,1460-38-4) → {(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)

Guidance literature:

Multi-step reaction with 12 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

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;

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

Reference yield:

[(1S,2R)-1-Allyl-2-((R)-2-hydroxy-1-methyl-ethyl)-cyclopentyl]-carbamic acid tert-butyl ester (250595-68-7) → {(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)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 95 percent / NEt₃; DMAP / CH₂Cl₂

2.1: 9-BBN / tetrahydrofuran

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

3.1: TFA / CH₂Cl₂

4.1: K₂CO₃ / H₂O

With dmap; 9-borabicyclo[3.3.1]nonane dimer; potassium carbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; 1.1: Etherification / 2.1: Addition / 2.2: Alkylation / 3.1: Deacylation / 4.1: Michael reaction;

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

Reference yield:

6a-allyl-2-oxo-hexahydro-cyclopenta[b]pyrrole-1-carboxylic acid tert-butyl ester (250595-65-4) → {(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)

Guidance literature:

Multi-step reaction with 8 steps

1.1: LiHMDS / tetrahydrofuran / -40 °C

1.2: 90 percent / tetrahydrofuran / -78 - 0 °C

2.1: 89 percent / LiOH; H₂O / tetrahydrofuran

3.1: NEt₃ / tetrahydrofuran

4.1: NaBH₄ / methanol

5.1: 95 percent / NEt₃; DMAP / CH₂Cl₂

6.1: 9-BBN / tetrahydrofuran

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

7.1: TFA / CH₂Cl₂

8.1: K₂CO₃ / H₂O

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: Metallation / 1.2: Methylation / 2.1: Hydrolysis / 3.1: Acylation / 4.1: Reduction / 5.1: Etherification / 6.1: Addition / 6.2: Alkylation / 7.1: Deacylation / 8.1: Michael reaction;

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

upstream raw materials:

(Z)-6-{(1R,2R)-1-Amino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-hex-2-enoic acid methyl ester

(2-oxocyclopent)acetic acid

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

(3aR,6aS)-6a-Allyl-hexahydro-cyclopenta[b]pyrrol-2-one

Downstream raw materials:

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

C₃₇H₅₃NO₃Si

C₃₇H₅₃NO₄Si

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