{(1S,5R,6S)-3-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(1S,5R,6S)-3-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester
• CAS No.: 392660-02-5
• Molecular Formula: C₂₁H₂₈FN₃O₅
• Molecular Weight: 421.469

Synonyms:

Chemical Property of {(1S,5R,6S)-3-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(1S,5R,6S)-3-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester

There total 6 articles about {(1S,5R,6S)-3-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester 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:

[(1S,5R,6S)-3-(2-Fluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-methyl-carbamic acid tert-butyl ester (392659-99-3) → {(1S,5R,6S)-3-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester (392660-02-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂ / Pd/C / methanol / 20 °C / 2844.31 Torr

2.1: NaHCO₃ / tetrahydrofuran

3.1: n-BuLi / tetrahydrofuran / 1.5 h / -78 °C

3.2: tetrahydrofuran

With n-butyllithium; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2005.06.063

Reference yield:

[(1α,5α,6α)-3-(2-fluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester (392659-98-2) → {(1S,5R,6S)-3-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester (392660-02-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 0 °C

2.1: H₂ / Pd/C / methanol / 20 °C / 2844.31 Torr

3.1: NaHCO₃ / tetrahydrofuran

4.1: n-BuLi / tetrahydrofuran / 1.5 h / -78 °C

4.2: tetrahydrofuran

With n-butyllithium; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2005.06.063

Reference yield:

3,4-difluoronitrobenzene (369-34-6) → {(1S,5R,6S)-3-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester (392660-02-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-ethyldiisopropylamine / acetonitrile / 80 °C

2.1: sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 0 °C

3.1: H₂ / Pd/C / methanol / 20 °C / 2844.31 Torr

4.1: NaHCO₃ / tetrahydrofuran

5.1: n-BuLi / tetrahydrofuran / 1.5 h / -78 °C

5.2: tetrahydrofuran

With n-butyllithium; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1016/j.bmcl.2005.06.063

upstream raw materials:

[(1S,5R,6S)-3-(4-Benzyloxycarbonylamino-2-fluoro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-methyl-carbamic acid tert-butyl ester

(R)-glycidyl butyrate

[(1S,5R,6S)-3-(2-Fluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-methyl-carbamic acid tert-butyl ester

[(1S,5R,6S)-3-(4-Amino-2-fluoro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-methyl-carbamic acid tert-butyl ester

Downstream raw materials:

Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester

N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-(N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide

{(1S,5R,6S)-3-[4-((S)-5-Aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester

{(1S,5R,6S)-3-[4-((R)-5-Azidomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester

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