3-[(1S,2R,4R)-7-Benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carbonyl]-(4S)-methyl-2-oxazolidinone

Base Information

Chemical Name:3-[(1S,2R,4R)-7-Benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carbonyl]-(4S)-methyl-2-oxazolidinone
CAS No.:1542980-57-3
Molecular Formula:C₁₉H₂₂N₂O₅
Molecular Weight:358.394
Hs Code.:

Synonyms:3-[(1S,2R,4R)-7-Benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carbonyl]-(4S)-methyl-2-oxazolidinone

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Chemical Property of 3-[(1S,2R,4R)-7-Benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carbonyl]-(4S)-methyl-2-oxazolidinone

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Technology Process of 3-[(1S,2R,4R)-7-Benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carbonyl]-(4S)-methyl-2-oxazolidinone

There total 3 articles about 3-[(1S,2R,4R)-7-Benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carbonyl]-(4S)-methyl-2-oxazolidinone 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%

: C₁₅H₁₆ClNO₃

: 4042-35-7
(S)-4-methyloxazolidin-2-one

: 1542980-48-2
3-[(1R,2S,4S)-7-benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carbonyl]-(4S)-methyl-2-oxazolidinone

: 1542980-57-3
3-[(1S,2R,4R)-7-Benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carbonyl]-(4S)-methyl-2-oxazolidinone

Guidance literature:: (S)-4-methyloxazolidin-2-one; With n-butyllithium; In tetrahydrofuran; at -50 ℃; for 1h; Inert atmosphere;

C₁₅H₁₆ClNO₃; In tetrahydrofuran; at -50 - -40 ℃; for 6h; Inert atmosphere;
DOI:10.1016/j.tetasy.2013.11.010

Reference yield:

: 7-[(benzyloxy)carbonyl]-7-azabicyclo[2.2.1]heptane-2-carboxylic acid

: 1542980-57-3
3-[(1S,2R,4R)-7-Benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carbonyl]-(4S)-methyl-2-oxazolidinone

Guidance literature:: Multi-step reaction with 2 steps

1.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 16 h / 20 °C / Cooling with ice; Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 1 h / -50 °C / Inert atmosphere

2.2: 6 h / -50 - -40 °C / Inert atmosphere

With n-butyllithium; thionyl chloride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetasy.2013.11.010

Reference yield:

: C₂₂H₂₃NO₄

: 1542980-57-3
3-[(1S,2R,4R)-7-Benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carbonyl]-(4S)-methyl-2-oxazolidinone

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydroxide / isopropyl alcohol / 1 h / Reflux

2.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 16 h / 20 °C / Cooling with ice; Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran / 1 h / -50 °C / Inert atmosphere

3.2: 6 h / -50 - -40 °C / Inert atmosphere

With n-butyllithium; thionyl chloride; N,N-dimethyl-formamide; sodium hydroxide; In tetrahydrofuran; dichloromethane; isopropyl alcohol;
DOI:10.1016/j.tetasy.2013.11.010