tert-butyl (1S,3R,5S)-3-[(benzylamino)methyl]-2-azabicyclo[3.1.0]hexane-2-carboxylate

Base Information

Chemical Name:tert-butyl (1S,3R,5S)-3-[(benzylamino)methyl]-2-azabicyclo[3.1.0]hexane-2-carboxylate
CAS No.:1266231-63-3
Molecular Formula:C₁₈H₂₆N₂O₂
Molecular Weight:302.417
Hs Code.:

Synonyms:tert-butyl (1S,3R,5S)-3-[(benzylamino)methyl]-2-azabicyclo[3.1.0]hexane-2-carboxylate

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Chemical Property of tert-butyl (1S,3R,5S)-3-[(benzylamino)methyl]-2-azabicyclo[3.1.0]hexane-2-carboxylate

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Technology Process of tert-butyl (1S,3R,5S)-3-[(benzylamino)methyl]-2-azabicyclo[3.1.0]hexane-2-carboxylate

There total 6 articles about tert-butyl (1S,3R,5S)-3-[(benzylamino)methyl]-2-azabicyclo[3.1.0]hexane-2-carboxylate 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:

: C₁₁H₁₇NO₃

: 100-46-9
benzylamine

: 1266231-63-3
tert-butyl (1S,3R,5S)-3-[(benzylamino)methyl]-2-azabicyclo[3.1.0]hexane-2-carboxylate

Guidance literature:: With sodium tris(acetoxy)borohydride; In tetrahydrofuran; at 20 ℃; for 18.5h;

Reference yield:

: 1452400-40-6
tert-butyl (2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-pyrrole-1-carboxylate

: 1266231-63-3
tert-butyl (1S,3R,5S)-3-[(benzylamino)methyl]-2-azabicyclo[3.1.0]hexane-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: diethylzinc / toluene / 0.5 h / -40 °C

1.2: 3 h / 0 - 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

3.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / ethyl acetate / 1 h / 0 - 20 °C

4.1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 18 h / 20 °C

With tetrabutyl ammonium fluoride; diethylzinc; sulfur trioxide pyridine complex; sodium tris(acetoxy)borohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethyl acetate; toluene;
DOI:10.1016/j.bmc.2013.07.020

Reference yield:

: 128811-31-4
tert-butyl (2R)-2-<<(tert-butyl)dimethylsilyloxy>methyl>-5-oxopyrrolidine-1-carboxylate

: 1266231-63-3
tert-butyl (1S,3R,5S)-3-[(benzylamino)methyl]-2-azabicyclo[3.1.0]hexane-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium triethylborohydride / toluene; tetrahydrofuran / 1 h / -70 °C

1.2: 1 h / 20 °C

2.1: diethylzinc / toluene / 0.5 h / -40 °C

2.2: 3 h / 0 - 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

4.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / ethyl acetate / 1 h / 0 - 20 °C

5.1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 18 h / 20 °C

With tetrabutyl ammonium fluoride; diethylzinc; sulfur trioxide pyridine complex; sodium tris(acetoxy)borohydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethyl acetate; toluene;
DOI:10.1016/j.bmc.2013.07.020