(4aR,5R,10aR)-8-Benzyl-5-methoxycarbonyloxy-9-oxo-3,4,4a,5,6,8,9,10-octahydro-pyrrolo[2,3-i]isoquinoline-2-carboxylic acid methyl ester

Base Information

Chemical Name:(4aR,5R,10aR)-8-Benzyl-5-methoxycarbonyloxy-9-oxo-3,4,4a,5,6,8,9,10-octahydro-pyrrolo[2,3-i]isoquinoline-2-carboxylic acid methyl ester
CAS No.:157035-29-5
Molecular Formula:C₂₂H₂₆N₂O₆
Molecular Weight:414.458
Hs Code.:

(4aR,5R,10aR)-8-Benzyl-5-methoxycarbonyloxy-9-oxo-3,4,4a,5,6,8,9,10-octahydro-pyrrolo[2,3-i]isoquinoline-2-carboxylic acid methyl ester

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Chemical Property of (4aR,5R,10aR)-8-Benzyl-5-methoxycarbonyloxy-9-oxo-3,4,4a,5,6,8,9,10-octahydro-pyrrolo[2,3-i]isoquinoline-2-carboxylic acid methyl ester

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Technology Process of (4aR,5R,10aR)-8-Benzyl-5-methoxycarbonyloxy-9-oxo-3,4,4a,5,6,8,9,10-octahydro-pyrrolo[2,3-i]isoquinoline-2-carboxylic acid methyl ester

There total 14 articles about (4aR,5R,10aR)-8-Benzyl-5-methoxycarbonyloxy-9-oxo-3,4,4a,5,6,8,9,10-octahydro-pyrrolo[2,3-i]isoquinoline-2-carboxylic acid methyl 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:

: (4aR,5R,8aR)-8a-(Benzylcarbamoyl-methyl)-5-methoxycarbonyloxy-8-oxo-octahydro-isoquinoline-2-carboxylic acid methyl ester

: 157035-29-5
(4aR,5R,10aR)-8-Benzyl-5-methoxycarbonyloxy-9-oxo-3,4,4a,5,6,8,9,10-octahydro-pyrrolo[2,3-i]isoquinoline-2-carboxylic acid methyl ester

Guidance literature:: With camphor-10-sulfonic acid; In chloroform; at 50 ℃; Yield given;
DOI:10.1016/S0040-4039(00)73333-8

Reference yield:

: 14429-02-8
benzyl-(4-methoxybenzyl)amine

: 157035-29-5
(4aR,5R,10aR)-8-Benzyl-5-methoxycarbonyloxy-9-oxo-3,4,4a,5,6,8,9,10-octahydro-pyrrolo[2,3-i]isoquinoline-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 10percent NaOH / CH₂Cl₂

2: NaI, CaCO₃ / acetone

3: 1.) LHMDS; 2.) Na₂S₂O₄

4: OsO₄, NaIO₄

5: NaB(OAc)3H

7: 75 percent / K₂CO₃ / H₂O; methanol; formic acid / 60 °C

8: benzene / Heating

9: CAN / methanol; H₂O

10: CSA / CHCl₃ / 50 °C

With sodium hydroxide; sodium periodate; osmium(VIII) oxide; sodium dithionite; ammonium cerium(IV) nitrate; camphor-10-sulfonic acid; sodium tris(acetoxy)borohydride; potassium carbonate; calcium carbonate; sodium iodide; lithium hexamethyldisilazane; In methanol; formic acid; dichloromethane; chloroform; water; acetone; benzene;
DOI:10.1016/S0040-4039(00)73333-8

Reference yield:

: 121651-99-8
(4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one

: 157035-29-5
(4aR,5R,10aR)-8-Benzyl-5-methoxycarbonyloxy-9-oxo-3,4,4a,5,6,8,9,10-octahydro-pyrrolo[2,3-i]isoquinoline-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 88 percent / TBDMSOTf, p-TsOH / acetone / -78 - 23 °C

2: 84 percent / DBU / benzene / Heating

3: 1.) LHMDS; 2.) Na₂S₂O₄

4: OsO₄, NaIO₄

5: NaB(OAc)3H

7: 75 percent / K₂CO₃ / H₂O; methanol; formic acid / 60 °C

8: benzene / Heating

9: CAN / methanol; H₂O

10: CSA / CHCl₃ / 50 °C

With sodium periodate; osmium(VIII) oxide; sodium dithionite; ammonium cerium(IV) nitrate; camphor-10-sulfonic acid; t-butyldimethylsiyl triflate; sodium tris(acetoxy)borohydride; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In methanol; formic acid; chloroform; water; acetone; benzene;
DOI:10.1016/S0040-4039(00)73333-8