[(1R,5S,7R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-6-(2,2,2-trifluoro-acetyl)-6-aza-spiro[4.5]dec-7-yl]-acetaldehyde

Base Information

• Chemical Name: [(1R,5S,7R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-6-(2,2,2-trifluoro-acetyl)-6-aza-spiro[4.5]dec-7-yl]-acetaldehyde
• CAS No.: 857685-74-6
• Molecular Formula: C₂₃H₃₀F₃NO₃
• Molecular Weight: 425.491
• Mol file: 857685-74-6.mol

Synonyms:[(1R,5S,7R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-6-(2,2,2-trifluoro-acetyl)-6-aza-spiro[4.5]dec-7-yl]-acetaldehyde

Chemical Property of [(1R,5S,7R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-6-(2,2,2-trifluoro-acetyl)-6-aza-spiro[4.5]dec-7-yl]-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,5S,7R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-6-(2,2,2-trifluoro-acetyl)-6-aza-spiro[4.5]dec-7-yl]-acetaldehyde

There total 20 articles about [(1R,5S,7R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-6-(2,2,2-trifluoro-acetyl)-6-aza-spiro[4.5]dec-7-yl]-acetaldehyde 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: 93.0%

(1R,5S,7R)-7-(2-hydroxyethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane (857685-72-4) → [(1R,5S,7R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-6-(2,2,2-trifluoro-acetyl)-6-aza-spiro[4.5]dec-7-yl]-acetaldehyde (857685-74-6)

Guidance literature:

With Celite; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo047882v

Reference yield:

(1R)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitrocyclopentane (857685-62-2) → [(1R,5S,7R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-6-(2,2,2-trifluoro-acetyl)-6-aza-spiro[4.5]dec-7-yl]-acetaldehyde (857685-74-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: Triton B / methanol; tetrahydrofuran; 2-methyl-propan-2-ol / 48 h / 20 °C

2.1: LiBH₄ / tetrahydrofuran / 24 h / 20 °C

3.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

4.1: sodium iodide; sodium hydrogen carbonate / acetone / 24 h / 20 °C

5.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 0.5 h / -78 °C

5.2: tetrahydrofuran; pentane / 3 h / -78 °C

6.1: iodine; sodium hydrogen carbonate / acetone; H₂O / 1 h / 0 °C

7.1: hydrogen; triethylamine / Raney nickel / cyclohexane / 4 h / 25 °C / 760.05 Torr

8.1: NaBH₄ / CH₂Cl₂; methanol / 0 - 20 °C

9.1: i-Pr₂NEt / 1,2-dichloro-ethane / 1 h / 0 °C

10.1: HF*pyridine complex / tetrahydrofuran / 20 °C

11.1: DMP / CH₂Cl₂ / 5 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; lithium borohydride; phthalic acid dimethyl ester; hydrogen; iodine; tert.-butyl lithium; N-benzyl-trimethylammonium hydroxide; sodium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; nickel; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; 1,2-dichloro-ethane; acetone; tert-butyl alcohol; pentane; 1.1: Michael addition;

DOI:10.1016/j.tet.2007.03.031

Reference yield:

Methanesulfonic acid 3-[(1S,2R)-2-((R)-2-benzyloxy-1-methyl-ethyl)-1-nitro-cyclopentyl]-propyl ester → [(1R,5S,7R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-6-(2,2,2-trifluoro-acetyl)-6-aza-spiro[4.5]dec-7-yl]-acetaldehyde (857685-74-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium iodide; sodium hydrogen carbonate / acetone / 24 h / 20 °C

2.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 0.5 h / -78 °C

2.2: tetrahydrofuran; pentane / 3 h / -78 °C

3.1: iodine; sodium hydrogen carbonate / acetone; H₂O / 1 h / 0 °C

4.1: hydrogen; triethylamine / Raney nickel / cyclohexane / 4 h / 25 °C / 760.05 Torr

5.1: NaBH₄ / CH₂Cl₂; methanol / 0 - 20 °C

6.1: i-Pr₂NEt / 1,2-dichloro-ethane / 1 h / 0 °C

7.1: HF*pyridine complex / tetrahydrofuran / 20 °C

8.1: DMP / CH₂Cl₂ / 5 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; phthalic acid dimethyl ester; hydrogen; iodine; tert.-butyl lithium; sodium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; nickel; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; 1,2-dichloro-ethane; acetone; pentane;

DOI:10.1016/j.tet.2007.03.031

upstream raw materials:

(1R,5S,7R)-7-(2-hydroxyethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane

(3R,3aR,6aR)-3-methyl-hexahydrocyclopenta[b]furan-2-one

(2R)-2-((1R)-2-benzyloxy-1-methylethyl)-cyclopentanone

(2R)-2-((1R)-2-benzyloxy-1-methylethyl)-cyclopentanone oxime

Downstream raw materials:

(1'R,5'S,7'R,1''R)-4-{1'-[2''-benzyloxy-1''-methyl-ethyl]-6'-trifluoroacetyl-6'-aza-5'-spiro[4.5]dec-7'-yl}-2-methylbut-2E-enoic acid ethyl ester