(R)-1-Benzyloxy-3-[(2R,3R)-3-(3,4-dimethoxy-phenyl)-2-hydroxymethyl-1-methyl-pyrrolidin-3-yl]-propan-2-ol

Base Information

• Chemical Name: (R)-1-Benzyloxy-3-[(2R,3R)-3-(3,4-dimethoxy-phenyl)-2-hydroxymethyl-1-methyl-pyrrolidin-3-yl]-propan-2-ol
• CAS No.: 131652-99-8
• Molecular Formula: C₂₄H₃₃NO₅
• Molecular Weight: 415.53
• Mol file: 131652-99-8.mol

Synonyms:(R)-1-Benzyloxy-3-[(2R,3R)-3-(3,4-dimethoxy-phenyl)-2-hydroxymethyl-1-methyl-pyrrolidin-3-yl]-propan-2-ol

Chemical Property of (R)-1-Benzyloxy-3-[(2R,3R)-3-(3,4-dimethoxy-phenyl)-2-hydroxymethyl-1-methyl-pyrrolidin-3-yl]-propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-Benzyloxy-3-[(2R,3R)-3-(3,4-dimethoxy-phenyl)-2-hydroxymethyl-1-methyl-pyrrolidin-3-yl]-propan-2-ol

There total 8 articles about (R)-1-Benzyloxy-3-[(2R,3R)-3-(3,4-dimethoxy-phenyl)-2-hydroxymethyl-1-methyl-pyrrolidin-3-yl]-propan-2-ol 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:

(R)-5-Benzyloxy-2-(3,4-dimethoxy-phenyl)-pentane-1,4-diol (131652-78-3,131723-78-9) → (R)-1-Benzyloxy-3-[(2R,3R)-3-(3,4-dimethoxy-phenyl)-2-hydroxymethyl-1-methyl-pyrrolidin-3-yl]-propan-2-ol (131652-99-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / n-Bu₃P / tetrahydrofuran / 1 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 0.5 h / -10 °C

3: CH₂Cl₂ / 5 h / Ambient temperature

4: 100 percent / 30percent H₂O₂ / CH₂Cl₂ / 9 h / 0 deg C to r.t.

5: 85 percent / xylene / 0.33 h / 250 °C / sealed tube

6: 88 percent / H₂ / 20percent Pd(OH)2-C / methanol / 8 h / Ambient temperature

7: 2) NaBH₄ / 1) MeOH, O deg C, 1h, 2) O deg C to r.t.

With sodium tetrahydroborate; tributylphosphine; hydrogen; dihydrogen peroxide; triethylamine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; dichloromethane; xylene;

DOI:10.1246/cl.1990.1239

Reference yield:

(R)-5-Benzyloxymethyl-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one (81309-80-0,81309-81-1) → (R)-1-Benzyloxy-3-[(2R,3R)-3-(3,4-dimethoxy-phenyl)-2-hydroxymethyl-1-methyl-pyrrolidin-3-yl]-propan-2-ol (131652-99-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / LiAlH₄ / tetrahydrofuran / 0.67 h / 0 °C

2: 94 percent / n-Bu₃P / tetrahydrofuran / 1 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 0.5 h / -10 °C

4: CH₂Cl₂ / 5 h / Ambient temperature

5: 100 percent / 30percent H₂O₂ / CH₂Cl₂ / 9 h / 0 deg C to r.t.

6: 85 percent / xylene / 0.33 h / 250 °C / sealed tube

7: 88 percent / H₂ / 20percent Pd(OH)2-C / methanol / 8 h / Ambient temperature

8: 2) NaBH₄ / 1) MeOH, O deg C, 1h, 2) O deg C to r.t.

With sodium tetrahydroborate; lithium aluminium tetrahydride; tributylphosphine; hydrogen; dihydrogen peroxide; triethylamine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; dichloromethane; xylene;

DOI:10.1246/cl.1990.1239

Reference yield:

(3aR,5R,7aR)-1-Benzyl-5-benzyloxymethyl-3a-(3,4-dimethoxy-phenyl)-hexahydro-pyrano[3,4-b]pyrrol-7-one (131652-97-6) → (R)-1-Benzyloxy-3-[(2R,3R)-3-(3,4-dimethoxy-phenyl)-2-hydroxymethyl-1-methyl-pyrrolidin-3-yl]-propan-2-ol (131652-99-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / H₂ / 20percent Pd(OH)2-C / methanol / 8 h / Ambient temperature

2: 2) NaBH₄ / 1) MeOH, O deg C, 1h, 2) O deg C to r.t.

With sodium tetrahydroborate; hydrogen; palladium hydroxide - carbon; In methanol;

DOI:10.1246/cl.1990.1239

upstream raw materials:

(3aR,5R,7aR)-5-Benzyloxymethyl-3a-(3,4-dimethoxy-phenyl)-hexahydro-pyrano[3,4-b]pyrrol-7-one

(R)-5-Benzyloxy-2-(3,4-dimethoxy-phenyl)-pentane-1,4-diol

(R)-5-Benzyloxymethyl-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one

(R)-1-Benzyloxy-4-(3,4-dimethoxy-phenyl)-5-(2-nitro-phenylselanyl)-pentan-2-ol

Downstream raw materials:

2,2-Dimethyl-propionic acid (3aR,7aS)-6-benzyloxy-3a-(3,4-dimethoxy-phenyl)-1-methyl-2,3,3a,4,5,7a-hexahydro-1H-indol-5-yl ester

Acetic acid (3aR,7aS)-6-benzyloxy-3a-(3,4-dimethoxy-phenyl)-1-methyl-2,3,3a,4,5,7a-hexahydro-1H-indol-5-yl ester

(3aR,7aS)-6-Benzyloxy-3a-(3,4-dimethoxy-phenyl)-1-methyl-2,3,3a,4,5,7a-hexahydro-1H-indol-5-ol

(3aR,7aS)-6-Benzyloxy-3a-(3,4-dimethoxy-phenyl)-1-methyl-1,2,3,3a,4,7a-hexahydro-indol-5-one

Refernces