(-)-methyl (1S,2R,3S,7aR)-hexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizine-1-carboxylate

Base Information

Chemical Name:(-)-methyl (1S,2R,3S,7aR)-hexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizine-1-carboxylate
CAS No.:935468-96-5
Molecular Formula:C₂₇H₂₈N₂O₃
Molecular Weight:428.531
Hs Code.:

Synonyms:(-)-methyl (1S,2R,3S,7aR)-hexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizine-1-carboxylate

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Chemical Property of (-)-methyl (1S,2R,3S,7aR)-hexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizine-1-carboxylate

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Technology Process of (-)-methyl (1S,2R,3S,7aR)-hexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizine-1-carboxylate

There total 5 articles about (-)-methyl (1S,2R,3S,7aR)-hexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizine-1-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: 83.0%

: 67-56-1
methanol

: 935468-93-2
(-)-(3aR,4S,8aR,8bS)-hexahydro-4-(naphthalen-2-yl)-2-(phenylmethyl)pyrrolo[3,4-a]pyrrolizine-1,3(2H,4H)-dione

: 935468-96-5
(-)-methyl (1S,2R,3S,7aR)-hexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizine-1-carboxylate

Guidance literature:: (-)-(3aR,4S,8aR,8bS)-hexahydro-4-(naphthalen-2-yl)-2-(phenylmethyl)pyrrolo[3,4-a]pyrrolizine-1,3(2H,4H)-dione; With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 15h;

methanol; With thionyl chloride; at 20 ℃; for 15h; Further stages.;
DOI:10.1002/hlca.200790028

Reference yield:

: 935468-92-1
(-)-S-methyl O-[(3aR,4S,7R,8aR,8bS)-decahydro-4-(naphthalen-2-yl)-1,3-dioxo-2-(phenylmethyl)pyrrolo[3,4-a]pyrrolizin-7-yl] dithiocarbonate

: 935468-96-5
(-)-methyl (1S,2R,3S,7aR)-hexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 88 percent / Bu₃SnH; AIBN / toluene / 1 h / Heating

2.1: NaOH / tetrahydrofuran; H₂O / 15 h / 20 °C

2.2: 83 percent / SOCl₂ / 15 h / 20 °C

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; water; toluene; 1.1: Barton-McCombie deoxygenation;
DOI:10.1002/hlca.200790028

Reference yield:

: 935468-53-4
(-)-(3aR,4S,7R,8aR,8bS)-hexahydro-7-hydroxy-4-(naphthalen-2-yl)-2-(phenylmethyl)pyrrolo[3,4-a]pyrrolizine-1,3(2H,4H)-dione

: 935468-96-5
(-)-methyl (1S,2R,3S,7aR)-hexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 3 h / 20 °C

1.2: tetrahydrofuran / 1 h / 20 °C

1.3: 84 percent / 17 h / 20 °C

2.1: 88 percent / Bu₃SnH; AIBN / toluene / 1 h / Heating

3.1: NaOH / tetrahydrofuran; H₂O / 15 h / 20 °C

3.2: 83 percent / SOCl₂ / 15 h / 20 °C

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; water; toluene; 2.1: Barton-McCombie deoxygenation;
DOI:10.1002/hlca.200790028