1-Azaspiro[4.5]decane-1-carboxylic acid, 6-(3-hydroxypropyl)-2-[(phenylmethoxy)methyl]-, 1,1-dimethylethyl ester, (2S,5S,6S)-

Base Information

• Chemical Name: 1-Azaspiro[4.5]decane-1-carboxylic acid, 6-(3-hydroxypropyl)-2-[(phenylmethoxy)methyl]-, 1,1-dimethylethyl ester, (2S,5S,6S)-
• CAS No.: 879572-77-7
• Molecular Formula: C25H39NO4
• Molecular Weight: 417.589
• Mol file: 879572-77-7.mol

Synonyms:

Chemical Property of 1-Azaspiro[4.5]decane-1-carboxylic acid, 6-(3-hydroxypropyl)-2-[(phenylmethoxy)methyl]-, 1,1-dimethylethyl ester, (2S,5S,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Azaspiro[4.5]decane-1-carboxylic acid, 6-(3-hydroxypropyl)-2-[(phenylmethoxy)methyl]-, 1,1-dimethylethyl ester, (2S,5S,6S)-

There total 3 articles about 1-Azaspiro[4.5]decane-1-carboxylic acid, 6-(3-hydroxypropyl)-2-[(phenylmethoxy)methyl]-, 1,1-dimethylethyl ester, (2S,5S,6S)- 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: 99.0%

(2S,5S,6S)-tert-butyl 2-(benzyloxymethyl)-6-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-aza-spiro[4,5]decane-1-carboxylate (879572-76-6) → (2S,5S,6S)-tert-butyl 2-(benzyloxymethyl)-6-(3'-hydroxypropyl)-1-azaspiro[4,5]decane-1-carboxylate (879572-77-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/ol053010j

Reference yield:

(2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate (879572-75-5) → (2S,5S,6S)-tert-butyl 2-(benzyloxymethyl)-6-(3'-hydroxypropyl)-1-azaspiro[4,5]decane-1-carboxylate (879572-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / hydrogen; triethylamine / Pd/C / methanol / 12 h / 20 °C

2: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

With tetrabutyl ammonium fluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/ol053010j

Reference yield:

(2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate (879572-72-2) → (2S,5S,6S)-tert-butyl 2-(benzyloxymethyl)-6-(3'-hydroxypropyl)-1-azaspiro[4,5]decane-1-carboxylate (879572-77-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / second generation Grubbs' catalyst / CH₂Cl₂ / 1 h / 40 °C

2: 95 percent / hydrogen; triethylamine / Pd/C / methanol / 12 h / 20 °C

3: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrabutyl ammonium fluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol053010j

upstream raw materials:

(2S,5S,6S)-tert-butyl 2-(benzyloxymethyl)-6-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-aza-spiro[4,5]decane-1-carboxylate

(2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate

(2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate

Downstream raw materials:

(3S,5S,7aS,11′S)-3-(benzyloxymethyl)-5-hexyldecahydro-1H-pyrrolo[1,2-j]quinoline

(2S,5S,7aS,11aS)-3-(benzyloxymethyl)decahydro-1H-pyrrolo[1,2-j]quinoline-5-carbonitrile

3-benzyloxymethyl-2,3,7,7a,8,9,10,11-octahydro-1H-pyrrolo[2,1-j]quinoline