(-)-N-benzyl-N-<(1R,2S,4S)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl> amine

Base Information

• Chemical Name: (-)-N-benzyl-N-<(1R,2S,4S)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl> amine
• CAS No.: 146389-05-1
• Molecular Formula: C₁₃H₁₄BrNO
• Molecular Weight: 280.164

Synonyms:(-)-N-benzyl-N-<(1R,2S,4S)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl> amine

Chemical Property of (-)-N-benzyl-N-<(1R,2S,4S)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl> amine

Chemical Property:

Purity/Quality:

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Technology Process of (-)-N-benzyl-N-<(1R,2S,4S)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl> amine

There total 6 articles about (-)-N-benzyl-N-<(1R,2S,4S)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl> amine 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: 49.0%

6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-one (146389-03-9) + benzylamine (100-46-9) → (1RS,2SR,4SR)-2-endo-benzylamino-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-exo-carbonitrile + (+/-)-N-benzyl-N-<(1RS,2SR,4SR)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl> amine (146352-62-7,146352-78-5,146389-05-1)

Guidance literature:

With methanesulfonic acid; 3 A molecular sieve; sodium cyanoborohydride; In methanol; for 14h;

DOI:10.1016/S0040-4020(01)88357-5

Reference yield: 14.0%

6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-one (146389-03-9) + benzylamine (100-46-9) → (1RS,2SR,4SR)-2-endo-benzylamino-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-exo-carbonitrile + (+/-)-N-benzyl-N-<(1RS,2SR,4SR)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl> amine (146352-62-7,146352-78-5,146389-05-1)

Guidance literature:

With methanesulfonic acid; 3 A molecular sieve; In methanol; for 14h;

DOI:10.1016/S0040-4020(01)88357-5

Reference yield:

Benzyl-[(1R,4S)-6-bromo-7-oxa-bicyclo[2.2.1]hept-5-en-(2E)-ylidene]-amine → (-)-N-benzyl-N-<(1R,2S,4S)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl> amine (146389-05-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; Yield given;

DOI:10.1016/S0040-4020(01)88357-5

upstream raw materials:

(1R,4S)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-one

benzylamine

6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-one

(+/-)-(1RS,2SR,4SR)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-endo-ol

Downstream raw materials:

(-)-benzyl N-benzyl,N-<(1R,2S,4S)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl>carbamate

benzyl N-benzyl,N-<(1R,2S,4S,5S)-5-exo-hydroxy-6-oxo-7-oxabicyclo<2.2.1>hept-2-endo-yl>carbamate

(+/-)-benzyl N-benzyl,N-<(1RS,2SR,4SR)-6-bromo-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl>carbamate

benzyl N-benzyl,N-<(1RS,2SR,4SR,5SR)-5-exo-hydroxy-6-oxo-7-oxabicyclo<2.2.1>hept-2-endo-yl>carbamate

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