(3S,8aS)-3-(4-Benzyloxy-butyl)-3-bromomethyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

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Chemical Name:(3S,8aS)-3-(4-Benzyloxy-butyl)-3-bromomethyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione
CAS No.:454439-62-4
Molecular Formula:C₁₉H₂₄BrNO₄
Molecular Weight:410.308
Hs Code.:

Synonyms:(3S,8aS)-3-(4-Benzyloxy-butyl)-3-bromomethyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

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Chemical Property of (3S,8aS)-3-(4-Benzyloxy-butyl)-3-bromomethyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

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Technology Process of (3S,8aS)-3-(4-Benzyloxy-butyl)-3-bromomethyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

There total 6 articles about (3S,8aS)-3-(4-Benzyloxy-butyl)-3-bromomethyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione 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: 60.0%

: 454439-61-3
(2S)-1-{2-[4-(benzyloxy)butyl]acryloyl}pyrrolidine-2-carboxylic acid

: 454439-62-4
(3S,8aS)-3-(4-Benzyloxy-butyl)-3-bromomethyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

Guidance literature:: With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1016/S0957-4166(02)00071-X

Reference yield:

: 60789-54-0
4-bromobutyl benzyl ether

: 454439-62-4
(3S,8aS)-3-(4-Benzyloxy-butyl)-3-bromomethyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / 1,2-dimethoxy-ethane / 2 h / 20 °C

1.2: 1,2-dimethoxy-ethane / 20 h / Heating

1.3: 55 percent / NaH / 1,2-dimethoxy-ethane / 4 h / 20 °C

2.1: 100 percent / KOH / methanol; H₂O / 6 h / Heating

3.1: 92 percent / DEPC; Et₃N / dimethylformamide / 2.5 h / 20 °C

4.1: 100 percent / KOH / methanol; H₂O / 4 h / 20 °C

5.1: 60 percent / NBS / dimethylformamide / 0 - 20 °C

With potassium hydroxide; N-Bromosuccinimide; sodium hydride; triethylamine; diethyl dicarbonate; In methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; 1.3: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/S0957-4166(02)00071-X

Reference yield:

: 5817-26-5
ethyl (2S)-pyrrolidine-2-carboxylate

: 454439-62-4
(3S,8aS)-3-(4-Benzyloxy-butyl)-3-bromomethyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / DEPC; Et₃N / dimethylformamide / 2.5 h / 20 °C

2: 100 percent / KOH / methanol; H₂O / 4 h / 20 °C

3: 60 percent / NBS / dimethylformamide / 0 - 20 °C

With potassium hydroxide; N-Bromosuccinimide; triethylamine; diethyl dicarbonate; In methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(02)00071-X