(R)-1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methylpyrrolidin-3-yl)ethan-1-ol

Base Information

• Chemical Name: (R)-1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methylpyrrolidin-3-yl)ethan-1-ol
• CAS No.: 884846-88-2
• Molecular Formula: C₂₁H₂₇NO₃
• Molecular Weight: 341.45
• Mol file: 884846-88-2.mol

Synonyms:(R)-1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methylpyrrolidin-3-yl)ethan-1-ol

Chemical Property of (R)-1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methylpyrrolidin-3-yl)ethan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methylpyrrolidin-3-yl)ethan-1-ol

There total 6 articles about (R)-1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methylpyrrolidin-3-yl)ethan-1-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: 64.0%

1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methyl-pyrrolidin-3-yl)ethanone (884846-87-1) → (R)-1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methylpyrrolidin-3-yl)ethan-1-ol (884846-88-2)

Guidance literature:

1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methyl-pyrrolidin-3-yl)ethanone; With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at -57 - -4.4 ℃;

In tetrahydrofuran; at 61 ℃; for 15h;

DOI:10.1021/ol060398p

Reference yield:

(E)-2-(benzyloxy)-1-methoxy-4-(2-nitrovinyl)benzene (63909-29-5) → (R)-1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methylpyrrolidin-3-yl)ethan-1-ol (884846-88-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: chiral bis(oxazoline)-based ligand; Mg(OTf)2; N-methylmorpholine / 4 Angstroem molecular sieves / CHCl₃; H₂O / 18 h / 20 °C

2.1: Zn dust; aq. HCl / ethanol / 45 - 52 °C

3.1: aq. NaHCO₃ / CH₂Cl₂

4.1: LiHMDS / toluene; tetrahydrofuran / 10 - 15 °C

5.1: pTSA / toluene / 90 °C

6.1: Li(t-BuO)3AlH / tetrahydrofuran / -57 - -4.4 °C

6.2: 64 percent / LiAkH₄ / tetrahydrofuran / 15 h / 61 °C

With 4-methyl-morpholine; hydrogenchloride; chiral bis(oxazoline)-based ligand; sodium hydrogencarbonate; toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; magnesium triflate; lithium hexamethyldisilazane; zinc; 4 A molecular sieve; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; toluene;

DOI:10.1021/ol060398p

Reference yield:

(3S,4S)-methyl 4-(3-(benzyloxy)-4-methoxyphenyl)-3-methyl-2-oxopyrrolidine-3-carboxylate (791807-34-6) → (R)-1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methylpyrrolidin-3-yl)ethan-1-ol (884846-88-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiHMDS / toluene; tetrahydrofuran / 10 - 15 °C

2.1: pTSA / toluene / 90 °C

3.1: Li(t-BuO)3AlH / tetrahydrofuran / -57 - -4.4 °C

3.2: 64 percent / LiAkH₄ / tetrahydrofuran / 15 h / 61 °C

With toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1021/ol060398p

upstream raw materials:

1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methyl-pyrrolidin-3-yl)ethanone

(3S,4S)-methyl 4-(3-(benzyloxy)-4-methoxyphenyl)-3-methyl-2-oxopyrrolidine-3-carboxylate

(S)-dimethyl 2-(1-(3-(benzyloxy)-4-methylphenyl)-2-nitroethyl)-2-methylmalonate

(E)-2-(benzyloxy)-1-methoxy-4-(2-nitrovinyl)benzene

Downstream raw materials:

Methyl 3-((1R)-1-hydroxyethyl)(3S,4S)-4-(3-hydroxy-4-methoxyphenyl)-3-methylpyrrolidinecarboxylate

1-((3S,4S)-4-(3-hydroxy-4-methoxyphenyl)-3-((R)-1-hydroxyethyl)-3-methyl-pyrrolidin-1-yl)-2-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)ethanone

1-((3S,4S)-3-((R)-1-hydroxyethyl)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methyl-pyrrolidin-1-yl)-2-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)ethanone