6-(3,3-dimethoxypropyl)-2-hydroxymethyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 6-(3,3-dimethoxypropyl)-2-hydroxymethyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester
• CAS No.: 438461-66-6
• Molecular Formula: C₂₃H₃₅NO₅
• Molecular Weight: 405.535
• Mol file: 438461-66-6.mol

Synonyms:

Chemical Property of 6-(3,3-dimethoxypropyl)-2-hydroxymethyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(3,3-dimethoxypropyl)-2-hydroxymethyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester

There total 10 articles about 6-(3,3-dimethoxypropyl)-2-hydroxymethyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl 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:

(2S,5S,6S)-2-Hydroxymethyl-6-(3-oxo-propyl)-1-aza-spiro[4.5]decane-1-carboxylic acid benzyl ester + trimethyl orthoformate (149-73-5) → 6-(3,3-dimethoxypropyl)-2-hydroxymethyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester (438461-66-6)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 0.833333h;

DOI:10.1021/jo0201070

Reference yield:

(S)-(-)-5-(Bromomethyl)-2-pyrrolidinone (72479-05-1) → 6-(3,3-dimethoxypropyl)-2-hydroxymethyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester (438461-66-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 92 percent / Li; CuCN / tetrahydrofuran / 19 h / -40 - -20 °C

2.1: 96 percent / KH / tetrahydrofuran / 0.92 h / 0 - 20 °C

3.1: t-BuLi / diethyl ether; pentane / 1.67 h / -78 - 20 °C

3.2: diethyl ether; pentane / 4 h / -78 - -20 °C

4.1: 828 mg / BF₃*2HOAc; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

5.1: BF₃*2AcOH / CH₂Cl₂ / 0.25 h / 20 °C

5.2: 89 percent / NaHCO₃; aq. H₂O₂ / methanol; tetrahydrofuran / Heating

6.1: H₂; Rh(CO)2acac; P(OPh)3 / tetrahydrofuran / 6 h / 60 °C / 3040.2 Torr

7.1: 466 mg / HCl / methanol / 0.83 h / 20 °C

With triphenyl phosphite; hydrogenchloride; acetylacetonatodicarbonylrhodium(l); 4 A molecular sieve; hydrogen; tert.-butyl lithium; boron trifluoride diacetate; lithium; potassium hydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane; 5.2: Tamao oxidation;

DOI:10.1021/jo0201070

Reference yield:

7-trimethylsilanylhept-5-en-1-ol (92121-08-9) → 6-(3,3-dimethoxypropyl)-2-hydroxymethyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester (438461-66-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 85 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 1.5 h / 0 - 20 °C

2.1: t-BuLi / diethyl ether; pentane / 1.67 h / -78 - 20 °C

2.2: diethyl ether; pentane / 4 h / -78 - -20 °C

3.1: 828 mg / BF₃*2HOAc; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

4.1: BF₃*2AcOH / CH₂Cl₂ / 0.25 h / 20 °C

4.2: 89 percent / NaHCO₃; aq. H₂O₂ / methanol; tetrahydrofuran / Heating

5.1: H₂; Rh(CO)2acac; P(OPh)3 / tetrahydrofuran / 6 h / 60 °C / 3040.2 Torr

6.1: 466 mg / HCl / methanol / 0.83 h / 20 °C

With 1H-imidazole; triphenyl phosphite; hydrogenchloride; acetylacetonatodicarbonylrhodium(l); 4 A molecular sieve; hydrogen; iodine; tert.-butyl lithium; boron trifluoride diacetate; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane; 4.2: Tamao oxidation;

DOI:10.1021/jo0201070

upstream raw materials:

trimethyl orthoformate

(S)-(-)-5-(Bromomethyl)-2-pyrrolidinone

7-trimethylsilanylhept-5-en-1-ol

benzyl chloroformate