(3S,11aS)-3-(3,4-Dimethoxy-benzyl)-1-hydroxy-8,9-dimethoxy-4-oxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

Base Information

Chemical Name:(3S,11aS)-3-(3,4-Dimethoxy-benzyl)-1-hydroxy-8,9-dimethoxy-4-oxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester
CAS No.:538367-18-9
Molecular Formula:C₂₇H₃₄N₂O₈
Molecular Weight:514.576
Hs Code.:

(3S,11aS)-3-(3,4-Dimethoxy-benzyl)-1-hydroxy-8,9-dimethoxy-4-oxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

Synonyms:(3S,11aS)-3-(3,4-Dimethoxy-benzyl)-1-hydroxy-8,9-dimethoxy-4-oxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

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Chemical Property of (3S,11aS)-3-(3,4-Dimethoxy-benzyl)-1-hydroxy-8,9-dimethoxy-4-oxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

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Technology Process of (3S,11aS)-3-(3,4-Dimethoxy-benzyl)-1-hydroxy-8,9-dimethoxy-4-oxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

There total 11 articles about (3S,11aS)-3-(3,4-Dimethoxy-benzyl)-1-hydroxy-8,9-dimethoxy-4-oxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester 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: 90.0%

: 538367-17-8
(3S,11aS)-3-(3,4-Dimethoxy-benzyl)-8,9-dimethoxy-1,4-dioxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

: 538367-18-9
(3S,11aS)-3-(3,4-Dimethoxy-benzyl)-1-hydroxy-8,9-dimethoxy-4-oxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

Guidance literature:: With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1016/S0040-4039(03)01785-4

Reference yield:

: 59-92-7,90638-38-3
levodopa

: 538367-18-9
(3S,11aS)-3-(3,4-Dimethoxy-benzyl)-1-hydroxy-8,9-dimethoxy-4-oxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 75 percent / H₂SO₄; water / 24 h

2.1: 99 percent / HCl / 6 h / Heating

3.1: Ac₂O / 4 h

3.2: 87 percent / water / methanol

4.1: 90 percent / K₂CO₃ / acetone / Heating

5.1: 85 percent / HCl / methanol / 4 h / Heating

6.1: 80 percent / bis(2-oxo-3-oxazolidinyl) phosphinic chloride; Et₃N / CH₂Cl₂ / 4 h

7.1: 86 percent / CF₃CO₂H / CH₂Cl₂ / 2 h

8.1: 80 percent / DMAP; Et₃N / CH₂Cl₂ / 6 h

9.1: 90 percent / Li(t-BuO)3AlH / tetrahydrofuran / 2 h / 0 °C

With hydrogenchloride; dmap; sulfuric acid; water; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; acetic anhydride; potassium carbonate; lithium tri-t-butoxyaluminum hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; acetone; 1.1: Pictet-Spengler cyclization;
DOI:10.1016/S0040-4039(03)01785-4

Reference yield:

: 138908-56-2
(S)-(+)-2-tert-butoxycarbonylamino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester

: 538367-18-9
(3S,11aS)-3-(3,4-Dimethoxy-benzyl)-1-hydroxy-8,9-dimethoxy-4-oxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / KOH; water / methanol

2: 80 percent / bis(2-oxo-3-oxazolidinyl) phosphinic chloride; Et₃N / CH₂Cl₂ / 4 h

3: 86 percent / CF₃CO₂H / CH₂Cl₂ / 2 h

4: 80 percent / DMAP; Et₃N / CH₂Cl₂ / 6 h

5: 90 percent / Li(t-BuO)3AlH / tetrahydrofuran / 2 h / 0 °C

With dmap; potassium hydroxide; water; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; lithium tri-t-butoxyaluminum hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4039(03)01785-4