(2R,6R)-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-(phenylmethyl)-2-(2-propen-1-yl)-2-piperidinemethanol

Base Information

• Chemical Name: (2R,6R)-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-(phenylmethyl)-2-(2-propen-1-yl)-2-piperidinemethanol
• CAS No.: 852118-99-1
• Molecular Formula: C₂₃H₃₉NO₂Si
• Molecular Weight: 389.654
• Mol file: 852118-99-1.mol

Synonyms:(2R,6R)-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-(phenylmethyl)-2-(2-propen-1-yl)-2-piperidinemethanol

Chemical Property of (2R,6R)-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-(phenylmethyl)-2-(2-propen-1-yl)-2-piperidinemethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R)-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-(phenylmethyl)-2-(2-propen-1-yl)-2-piperidinemethanol

There total 2 articles about (2R,6R)-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-(phenylmethyl)-2-(2-propen-1-yl)-2-piperidinemethanol 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: 87.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,6R)-1-(phenylmethyl)-2-(2-propen-1-yl)-2,6-piperidinedimethanol (820967-79-1) → (2R,6R)-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-(phenylmethyl)-2-(2-propen-1-yl)-2-piperidinemethanol (852118-99-1)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; for 0.666667h;

DOI:10.1016/j.tetlet.2005.02.133

Reference yield:

(2R,6R)-1-(phenylmethyl)-2-(2-propen-1-yl)-2,6-piperidinedicarboxylic acid dimethyl ester (246245-91-0) → (2R,6R)-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-(phenylmethyl)-2-(2-propen-1-yl)-2-piperidinemethanol (852118-99-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / LiAlH₄ / tetrahydrofuran / 5 h / 0 °C

2: 87 percent / imidazole; DMAP / CH₂Cl₂ / 0.67 h

With 1H-imidazole; dmap; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2005.02.133

Reference yield:

(2R,6R)-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-(phenylmethyl)-2-(2-propen-1-yl)-2-piperidinemethanol (852118-99-1) → (5R,7R)-6-Benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-6-aza-spiro[4.5]dec-2-en-1-ol (852119-05-2)

Guidance literature:

Multi-step reaction with 3 steps

1: DMSO; (COCl)2

2: tetrahydrofuran / 0.5 h / -20 °C

3: 95 percent / Grubbs II catalyst / CH₂Cl₂ / 4 h / 35 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 1: Swern oxidation;

DOI:10.1016/j.tetlet.2005.02.133

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,6R)-1-(phenylmethyl)-2-(2-propen-1-yl)-2,6-piperidinedimethanol

(2R,6R)-1-(phenylmethyl)-2-(2-propen-1-yl)-2,6-piperidinedicarboxylic acid dimethyl ester

Downstream raw materials:

(2R,6R)-2-Allyl-1-benzyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidine-2-carbaldehyde

(5R,7R)-6-Benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-6-aza-spiro[4.5]dec-2-en-1-ol

1-[(2R,6R)-2-Allyl-1-benzyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidin-2-yl]-prop-2-en-1-ol