tert-butyl (2S)-2-[(1S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate

Base Information

Chemical Name:tert-butyl (2S)-2-[(1S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate
CAS No.:1187849-25-7
Molecular Formula:C₂₀H₂₉NO₃
Molecular Weight:331.455
Hs Code.:

Synonyms:tert-butyl (2S)-2-[(1S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate

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Chemical Property of tert-butyl (2S)-2-[(1S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate

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Technology Process of tert-butyl (2S)-2-[(1S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate

There total 6 articles about tert-butyl (2S)-2-[(1S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate 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: 92.0%

: 1187849-24-6
tert-butyl N-allyl-N-{(1S)-1-[(1S)-1-(benzyloxy)propyl]-3-butenyl}carbamate

: 1187849-25-7
tert-butyl (2S)-2-[(1S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate

Guidance literature:: With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/j.tet.2009.06.060

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 1187849-25-7
tert-butyl (2S)-2-[(1S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 0 - 20 °C

2: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 50 °C

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3: |Cross Metathesis;
DOI:10.1016/j.tet.2017.12.024

Reference yield:

: 100-39-0
benzyl bromide

: 1187849-25-7
tert-butyl (2S)-2-[(1S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C

1.2: 0 - 20 °C

2.1: water; ammonium cerium (IV) nitrate / acetonitrile / 0 - 20 °C

3.1: triethylamine / dichloromethane / 0 - 20 °C

4.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 50 °C

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; ammonium cerium (IV) nitrate; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 5.1: |Cross Metathesis;
DOI:10.1016/j.tet.2017.12.024