(1S,3S)-N-(1-methylbenzyl)-3-isopropenyl-5-hydroxypentamide

Base Information

• Chemical Name: (1S,3S)-N-(1-methylbenzyl)-3-isopropenyl-5-hydroxypentamide
• CAS No.: 864182-75-2
• Molecular Formula: C₁₆H₂₃NO₂
• Molecular Weight: 261.364
• Mol file: 864182-75-2.mol

Synonyms:(1S,3S)-N-(1-methylbenzyl)-3-isopropenyl-5-hydroxypentamide

Chemical Property of (1S,3S)-N-(1-methylbenzyl)-3-isopropenyl-5-hydroxypentamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S)-N-(1-methylbenzyl)-3-isopropenyl-5-hydroxypentamide

There total 2 articles about (1S,3S)-N-(1-methylbenzyl)-3-isopropenyl-5-hydroxypentamide 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: 42.0%

(3RS)-3-(isopropenyl)pentanolide (864182-74-1) + (S)-1-phenyl-ethylamine (2627-86-3) → (1S,3S)-N-(1-methylbenzyl)-3-isopropenyl-5-hydroxypentamide (864182-75-2) + (1S,3R)-N-(1-methylbenzyl)-3-isopropenyl-5-hydroxypentamide

Guidance literature:

(S)-1-phenyl-ethylamine; With trimethylaluminum; In hexane; dichloromethane; at 0 ℃; for 0.25h;

(3RS)-3-(isopropenyl)pentanolide; In hexane; dichloromethane; at 20 ℃; for 16h;

DOI:10.1039/b504545b

Reference yield:

5,6-dihydro-pyran-2-one (3393-45-1) → (1S,3S)-N-(1-methylbenzyl)-3-isopropenyl-5-hydroxypentamide (864182-75-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: t-BuLi / tetrahydrofuran / 0.5 h / -78 °C

1.2: CuCN / tetrahydrofuran / 0.5 h / -78 - -40 °C

1.3: 58 percent / tetrahydrofuran / -78 - -40 °C

2.1: Me₃Al / hexane; CH₂Cl₂ / 0.25 h / 0 °C

2.2: 39 percent / hexane; CH₂Cl₂ / 16 h / 20 °C

With trimethylaluminum; tert.-butyl lithium; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1039/b504545b

Reference yield:

(1S,3S)-N-(1-methylbenzyl)-3-isopropenyl-5-hydroxypentamide (864182-75-2) → (E)-4-{(R)-4-[(R)-1-Acetoxy-4-methyl-3-(5-methylene-2-phenyl-[1,3]dioxan-4-ylmethyl)-pent-4-enyl]-5-oxo-2,5-dihydro-furan-2-yl}-3-methyl-but-2-enoic acid (864270-19-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 85 percent / pyridinium p-toluenesulfonate / toluene / 16 h / Heating

2.1: 88 percent / DIBAL / tetrahydrofuran; toluene / 0.5 h / -78 °C

3.1: t-BuLi / pentane; diethyl ether / -78 - 0 °C

3.2: 64 percent / pentane; diethyl ether / 0 - 20 °C

4.1: 64 percent / pyridinium p-toluenesulfonate / benzene / 2 h / Heating

5.1: 95 percent / dimethyl sulfoxide; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

6.2: 60 percent / tetrahydrofuran; hexane / 1 h / -78 °C

7.1: 96 percent / aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

8.1: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 °C

9.1: 50 percent / pyridinium p-toluenesulfonate; MeOH / benzene / 72 h / 20 °C

10.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

11.1: aq. NaClO₂; KH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 7 h / 20 °C

With methanol; dmap; sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; tert-butyl alcohol; pentane; benzene; 5.1: Swern oxidation;

DOI:10.1039/b504545b

upstream raw materials:

(3RS)-3-(isopropenyl)pentanolide

(S)-1-phenyl-ethylamine

5,6-dihydro-pyran-2-one

Downstream raw materials:

(3S)-3-isopropenyl-5,7-O-benzylidene-6-(methylene)heptanal

(3S)-3-isopropenyl-5,7-O-benzylidene-6-methylene-heptanol

(3R)-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]-1-{5-[(2E)-2-methyl-4-oxobut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}pent-4-enyl acetate

(3R)-1-{5-[(2E)-4-hydroxy-2-methylbut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl acetate