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

Base Information

• Chemical Name: 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
• CAS No.: 884846-89-3
• Molecular Formula: C₃₃H₄₇NO₅
• Molecular Weight: 537.74
• Mol file: 884846-89-3.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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:

(E)-2-(benzyloxy)-1-methoxy-4-(2-nitrovinyl)benzene (63909-29-5) → 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 (884846-89-3)

Guidance literature:

Multi-step reaction with 7 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

7.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

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

DOI:10.1021/ol060398p

Reference yield:

(R)-1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methylpyrrolidin-3-yl)ethan-1-ol (884846-88-2) + L-menthoxyacetyl chloride (15356-62-4) → 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 (884846-89-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/ol060398p

Reference yield:

1-((3S,4S)-4-(3-(benzyloxy)-4-methoxyphenyl)-3-methyl-pyrrolidin-3-yl)ethanone (884846-87-1) → 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 (884846-89-3)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 64 percent / LiAkH₄ / tetrahydrofuran / 15 h / 61 °C

2.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

With lithium tri-t-butoxyaluminum hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol060398p

upstream raw materials:

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

L-menthoxyacetyl chloride

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

Downstream raw materials:

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