ethyl 2-bromo-3-[4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(2S)-pyrrolidine-2-methoxy]phenyl]propanoate

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Chemical Name:ethyl 2-bromo-3-[4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(2S)-pyrrolidine-2-methoxy]phenyl]propanoate
CAS No.:199109-34-7
Molecular Formula:C₃₇H₄₆BrNO₅
Molecular Weight:664.68
Hs Code.:

Synonyms:ethyl 2-bromo-3-[4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(2S)-pyrrolidine-2-methoxy]phenyl]propanoate

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Chemical Property of ethyl 2-bromo-3-[4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(2S)-pyrrolidine-2-methoxy]phenyl]propanoate

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Technology Process of ethyl 2-bromo-3-[4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(2S)-pyrrolidine-2-methoxy]phenyl]propanoate

There total 6 articles about ethyl 2-bromo-3-[4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(2S)-pyrrolidine-2-methoxy]phenyl]propanoate 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: 47.0%

: 140-88-5,9003-32-1
ethyl acrylate

: 199109-29-0
4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(2S)-pyrrolidine-2-methoxy]aniline

: 199109-34-7
ethyl 2-bromo-3-[4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(2S)-pyrrolidine-2-methoxy]phenyl]propanoate

Guidance literature:: 4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(2S)-pyrrolidine-2-methoxy]aniline; With hydrogen bromide; sodium nitrite; In methanol; acetone; at 0 ℃; for 0.5h;

ethyl acrylate; With copper(I) oxide; In methanol; acetone; at 38 ℃;
DOI:10.1021/jm9805541

Reference yield:

: 100-02-7,78813-13-5,89830-32-0
4-nitro-phenol

: 199109-34-7
ethyl 2-bromo-3-[4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(2S)-pyrrolidine-2-methoxy]phenyl]propanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 0.5 h / 25 °C

1.2: 81 percent / dimethylformamide / 2 h / 25 °C

2.1: 91 percent / H₂ / 10 percent Pd/C / ethyl acetate / 6 h / 25 °C / 3102.89 Torr

3.1: NaNO₂; aq. HBr / methanol; acetone / 0.5 h / 0 °C

3.2: 47 percent / Cu₂O / methanol; acetone / 38 °C

With hydrogen bromide; hydrogen; sodium hydride; sodium nitrite; palladium on activated charcoal; In methanol; ethyl acetate; N,N-dimethyl-formamide; acetone; 1.1: Metallation / 1.2: Substitution / 2.1: Catalytic hydrogenation / 3.1: Diazotization / 3.2: Substitution;
DOI:10.1021/jm9805541

Reference yield:

: 171270-07-8
(6-Benzyloxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methanol

: 199109-34-7
ethyl 2-bromo-3-[4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(2S)-pyrrolidine-2-methoxy]phenyl]propanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

2.1: 75 percent / 6 h / 120 °C

3.1: NaH / dimethylformamide / 0.5 h / 25 °C

3.2: 81 percent / dimethylformamide / 2 h / 25 °C

4.1: 91 percent / H₂ / 10 percent Pd/C / ethyl acetate / 6 h / 25 °C / 3102.89 Torr

5.1: NaNO₂; aq. HBr / methanol; acetone / 0.5 h / 0 °C

5.2: 47 percent / Cu₂O / methanol; acetone / 38 °C

With hydrogen bromide; hydrogen; sodium hydride; triethylamine; sodium nitrite; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; 1.1: mesylation / 2.1: Substitution / 3.1: Metallation / 3.2: Substitution / 4.1: Catalytic hydrogenation / 5.1: Diazotization / 5.2: Substitution;
DOI:10.1021/jm9805541