tert-butyl (1S,4S)-4-[4-(benzyloxy)benzyl]-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

Base Information

Chemical Name:tert-butyl (1S,4S)-4-[4-(benzyloxy)benzyl]-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate
CAS No.:1449602-36-1
Molecular Formula:C₂₄H₂₇NO₅
Molecular Weight:409.482
Hs Code.:

Synonyms:tert-butyl (1S,4S)-4-[4-(benzyloxy)benzyl]-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

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Chemical Property of tert-butyl (1S,4S)-4-[4-(benzyloxy)benzyl]-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

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Technology Process of tert-butyl (1S,4S)-4-[4-(benzyloxy)benzyl]-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

There total 4 articles about tert-butyl (1S,4S)-4-[4-(benzyloxy)benzyl]-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-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: 50.0%

: 1-tert-butyl 2-methyl (4S)-2-[4-(benzyloxy)benzyl]-4-hydroxypyrrolidine-1,2-dicarboxylate

: 1449602-36-1
tert-butyl (1S,4S)-4-[4-(benzyloxy)benzyl]-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

Guidance literature:: 1-tert-butyl 2-methyl (4S)-2-[4-(benzyloxy)benzyl]-4-hydroxypyrrolidine-1,2-dicarboxylate; With sodium hydroxide; In methanol; water; for 4h; Reflux;

With dmap; dicyclohexyl-carbodiimide; In chloroform; at 0 ℃; for 10h;
DOI:10.3987/COM-12-S(N)9

Reference yield:

: 367966-45-8
(2S,4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester

: 1449602-36-1
tert-butyl (1S,4S)-4-[4-(benzyloxy)benzyl]-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

1.2: 5 h / 0 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C

3.1: sodium hydroxide / methanol; water / 4 h / Reflux

3.2: 10 h / 0 °C

With tetrabutyl ammonium fluoride; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water;
DOI:10.3987/COM-12-S(N)9

Reference yield:

: 1-tert-butyl 2-methyl (4S)-2-[4-(benzyloxy)benzyl]-4-{[tert-butyl(dimethyl)silyl]oxy}-pyrrolidine-1,2-dicarboxylate

: 1449602-36-1
tert-butyl (1S,4S)-4-[4-(benzyloxy)benzyl]-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C

2.1: sodium hydroxide / methanol; water / 4 h / Reflux

2.2: 10 h / 0 °C

With tetrabutyl ammonium fluoride; sodium hydroxide; In tetrahydrofuran; methanol; water;
DOI:10.3987/COM-12-S(N)9