tert-butyl (S)-1-<1-<2-(N,N-dibenzylamino)-4-bromobutyl>>-3-hydroxypyrrole-2-carboxylate

Base Information

Chemical Name:tert-butyl (S)-1-<1-<2-(N,N-dibenzylamino)-4-bromobutyl>>-3-hydroxypyrrole-2-carboxylate
CAS No.:159497-97-9
Molecular Formula:C₂₇H₃₃BrN₂O₃
Molecular Weight:513.475
Hs Code.:

Synonyms:tert-butyl (S)-1-<1-<2-(N,N-dibenzylamino)-4-bromobutyl>>-3-hydroxypyrrole-2-carboxylate

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Chemical Property of tert-butyl (S)-1-<1-<2-(N,N-dibenzylamino)-4-bromobutyl>>-3-hydroxypyrrole-2-carboxylate

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Technology Process of tert-butyl (S)-1-<1-<2-(N,N-dibenzylamino)-4-bromobutyl>>-3-hydroxypyrrole-2-carboxylate

There total 10 articles about tert-butyl (S)-1-<1-<2-(N,N-dibenzylamino)-4-bromobutyl>>-3-hydroxypyrrole-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: 80.0%

: 159497-96-8
tert-butyl (S)-1-<1-<2-(N,N-dibenzylamino)-4-hydroxybutyl>>-3-hydroxypyrrole-2-carboxylate

: 159497-97-9
tert-butyl (S)-1-<1-<2-(N,N-dibenzylamino)-4-bromobutyl>>-3-hydroxypyrrole-2-carboxylate

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 ℃; for 0.0833333h;
DOI:10.1021/jo00101a042

Reference yield:

: 137428-32-1
(2S)-2-[bis(phenylmethyl)amino]-1,4-butanediol

: 159497-97-9
tert-butyl (S)-1-<1-<2-(N,N-dibenzylamino)-4-bromobutyl>>-3-hydroxypyrrole-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 66 percent / imidazole / dimethylformamide / 2 h / 0 °C

2: 94 percent / MesCl, Et₃N / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) 1 h

3: 52 percent / tetrahydrofuran / 48 h / 50 °C

4: 95 percent / hydrazine hydrate / ethanol / 16 h / Heating

5: 95 percent / 2 N NaOH / ethanol / 24 h / 60 °C

6: 2.) silica gel / 1.) CH₂Cl₂, r.t., 16 h, 2.) 16 h

7: 80 percent / CBr₄, Ph₃P / CH₂Cl₂ / 0.08 h / 0 °C

With 1H-imidazole; sodium hydroxide; carbon tetrabromide; silica gel; hydrazine hydrate; methanesulfonyl chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00101a042

Reference yield:

: 152299-13-3
(2S)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(dibenzylamino)butan-1-ol

: 159497-97-9
tert-butyl (S)-1-<1-<2-(N,N-dibenzylamino)-4-bromobutyl>>-3-hydroxypyrrole-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / MesCl, Et₃N / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) 1 h

2: 52 percent / tetrahydrofuran / 48 h / 50 °C

3: 95 percent / hydrazine hydrate / ethanol / 16 h / Heating

4: 95 percent / 2 N NaOH / ethanol / 24 h / 60 °C

5: 2.) silica gel / 1.) CH₂Cl₂, r.t., 16 h, 2.) 16 h

6: 80 percent / CBr₄, Ph₃P / CH₂Cl₂ / 0.08 h / 0 °C

With sodium hydroxide; carbon tetrabromide; silica gel; hydrazine hydrate; methanesulfonyl chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jo00101a042