(1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

Base Information

• Chemical Name: (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one
• CAS No.: 446246-12-4
• Molecular Formula: C₂₃H₃₃NO₃S
• Molecular Weight: 403.586
• Mol file: 446246-12-4.mol

Synonyms:(1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

Chemical Property of (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

There total 13 articles about (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 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: 51.0%

pivalaldehyde (630-19-3) + (1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (446246-08-8) → (1R,2S,6R,7S)-5-[(1R,2R)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one + (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (446246-12-4)

Guidance literature:

(1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.583333h;

pivalaldehyde; In tetrahydrofuran; hexane; at -100 ℃; for 1h;

DOI:10.1016/S0957-4166(02)00043-5

Reference yield:

(1R,2S,6R,7S)-1,10,10-trimethyl-5-[(1R)-2-oxo-3,3-dimethyl-1-(phenylsulfanyl)butyl]-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (446246-15-7) → (1R,2S,6R,7S)-5-[(1R,2R)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one + (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (446246-12-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; water; at 25 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(02)00043-5

Reference yield:

(1R,2S,6R,7S)-(-)-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (41719-63-5,141117-60-4,141117-61-5,131897-87-5) → (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (446246-12-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 72 percent / sodium hydride; Bu₄NI / tetrahydrofuran / 6 h / Heating

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 °C

2.2: 72 percent / tetrahydrofuran; hexane / 1 h / -100 °C

3.1: 80 percent / mercuric acetate; aqueous acetic acid; calcium carbonate / 80 °C / pH 7

4.1: p-toluenesulfonic acid / benzene / 0.5 h / 25 °C

4.2: 78 percent / benzene / 8 h / Heating

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 °C

5.2: 51 percent / tetrahydrofuran; hexane / 1 h / -100 °C

With n-butyllithium; mercury(II) diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; calcium carbonate; In tetrahydrofuran; hexane; benzene; 2.2: Corey-Seebach reaction / 5.2: Corey-Seebach reaction;

DOI:10.1016/S0957-4166(02)00043-5

upstream raw materials:

pivalaldehyde

(1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

(1R,2S,6R,7S)-1,10,10-trimethyl-5-[(1R)-2-oxo-3,3-dimethyl-1-(phenylsulfanyl)butyl]-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

phenylthiomethyl chloride

Downstream raw materials:

(1R,2S,6R,7S)-5-[(1R,2R)-2-hydroxy-2-phenyl-1-(phenylsulfanyl)ethyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

(1R,2S,6R,7S)-5-[(1R,2R)-2-hydroxy-2-cyclohexyl-1-(phenylsulfanyl)ethyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

(1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

(S)-2-hydroxy-3,3-dimethylbutanoic acid