(+)-(1S,2S,3R,4R,5S)-5-endo-benzylamino-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane

Base Information

Chemical Name:(+)-(1S,2S,3R,4R,5S)-5-endo-benzylamino-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane
CAS No.:573717-07-4
Molecular Formula:C₂₁H₃₀N₂O₄
Molecular Weight:374.48
Hs Code.:

Synonyms:(+)-(1S,2S,3R,4R,5S)-5-endo-benzylamino-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane

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Chemical Property of (+)-(1S,2S,3R,4R,5S)-5-endo-benzylamino-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane

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Technology Process of (+)-(1S,2S,3R,4R,5S)-5-endo-benzylamino-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane

There total 10 articles about (+)-(1S,2S,3R,4R,5S)-5-endo-benzylamino-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane 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: 56.0%

: 100-52-7
benzaldehyde

: 573716-99-1
(+)-(1S,2S,3R,4R,5S)-5-endo-amino-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane

: 573717-07-4
(+)-(1S,2S,3R,4R,5S)-5-endo-benzylamino-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane

Guidance literature:: With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 25 ℃; for 1h;
DOI:10.1021/jo0301088

Reference yield:

: 227454-54-8
5-oxo-6-(toluene-4-sulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester

: 573717-07-4
(+)-(1S,2S,3R,4R,5S)-5-endo-benzylamino-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 10 steps

1: 85 percent / LiBH₄ / tetrahydrofuran / 0.25 h / -78 °C

2: 44 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

3: 90 percent / NaOMe / methanol; tetrahydrofuran / 4 h / 0 °C / pH 8

4: 82 percent / OsO₄; morpholine N-oxide / acetone; H₂O; CCl₄ / 2 h

5: 82 percent / p-toluenesulfonic acid monohydrate / acetone / 0.13 h / 20 °C

6: 87 percent / DMAP; pyridine / 12 h

7: trimethylsilyl azide; Bu₄NF / tetrahydrofuran / 75 °C

8: H₂ / Pd/C / methanol / 0.5 h / 20 °C / atmospheric pressure

9: sodium amalgam / tetrahydrofuran; methanol / 1.5 h

10: 56 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 1 h / 25 °C

With pyridine; 4-morpholinyl-N-oxide; dmap; sodium amalgam; osmium(VIII) oxide; lithium borohydride; trimethylsilylazide; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; 1,2-dichloro-ethane; acetone;
DOI:10.1021/jo0301088

Reference yield:

: 573716-66-2
tert-butyl (1R,4S,5R,6S)-5-hydroxy-6-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate

: 573717-07-4
(+)-(1S,2S,3R,4R,5S)-5-endo-benzylamino-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / OsO₄; morpholine N-oxide / acetone; H₂O; CCl₄ / 2 h

2: 82 percent / p-toluenesulfonic acid monohydrate / acetone / 0.13 h / 20 °C

3: 87 percent / DMAP; pyridine / 12 h

4: trimethylsilyl azide; Bu₄NF / tetrahydrofuran / 75 °C

5: H₂ / Pd/C / methanol / 0.5 h / 20 °C / atmospheric pressure

6: sodium amalgam / tetrahydrofuran; methanol / 1.5 h

7: 56 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 1 h / 25 °C

With pyridine; 4-morpholinyl-N-oxide; dmap; sodium amalgam; osmium(VIII) oxide; trimethylsilylazide; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; water; 1,2-dichloro-ethane; acetone;
DOI:10.1021/jo0301088