1-[4-((5R)-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

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Chemical Name:1-[4-((5R)-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester
CAS No.:1259556-27-8
Molecular Formula:C₂₀H₂₆N₂O₅
Molecular Weight:374.437
Hs Code.:

Synonyms:1-[4-((5R)-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

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Chemical Property of 1-[4-((5R)-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

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Technology Process of 1-[4-((5R)-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

There total 7 articles about 1-[4-((5R)-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-3-carboxylic 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: 96.0%

: 1259556-26-7
1-(4-benzyloxycarbonylamino-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

: 60456-26-0
(R)-glycidyl butyrate

: 1259556-27-8
1-[4-((5R)-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

Guidance literature:: 1-(4-benzyloxycarbonylamino-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

(R)-glycidyl butyrate; In tetrahydrofuran; hexane; at -78 - 20 ℃;

Reference yield:

: 16532-79-9
4-Bromophenylacetonitrile

: 1259556-27-8
1-[4-((5R)-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -10 °C

1.2: 4 h / -10 - 20 °C

2.1: dimethylsulfide borane complex; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 80 °C

2.2: 0 °C

2.3: pH 8

3.1: thionyl chloride / 1,1-dichloroethane / 2 h / 0 - 20 °C

3.2: 0 °C / pH 8

4.1: triethylamine / dichloromethane / 2 h / 0 °C

5.1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 4 h / Reflux

6.1: hydrogen / palladium 10% on activated carbon / methanol

7.1: sodium hydrogencarbonate / toluene; water; acetone / 0 - 20 °C

8.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

8.2: -78 - 20 °C

With n-butyllithium; thionyl chloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; methanol; 1,1-dichloroethane; hexane; dichloromethane; water; acetone; toluene;

Reference yield:

: 86215-40-9
1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexane

: 1259556-27-8
1-[4-((5R)-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 2 h / 0 °C

2.1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 4 h / Reflux

3.1: hydrogen / palladium 10% on activated carbon / methanol

4.1: sodium hydrogencarbonate / toluene; water; acetone / 0 - 20 °C

5.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

5.2: -78 - 20 °C

With n-butyllithium; hydrogen; sodium hydrogencarbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; toluene;