(-)-(1S,2R,3S,7aR)-hexahydro-1-(hydroxymethyl)-3-(naphthalen-2-yl)-N-(phenylmethyl)-1H-pyrrolizine-2-carboxamide

Base Information

Chemical Name:(-)-(1S,2R,3S,7aR)-hexahydro-1-(hydroxymethyl)-3-(naphthalen-2-yl)-N-(phenylmethyl)-1H-pyrrolizine-2-carboxamide
CAS No.:935468-99-8
Molecular Formula:C₂₆H₂₈N₂O₂
Molecular Weight:400.521
Hs Code.:

Synonyms:(-)-(1S,2R,3S,7aR)-hexahydro-1-(hydroxymethyl)-3-(naphthalen-2-yl)-N-(phenylmethyl)-1H-pyrrolizine-2-carboxamide

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Chemical Property of (-)-(1S,2R,3S,7aR)-hexahydro-1-(hydroxymethyl)-3-(naphthalen-2-yl)-N-(phenylmethyl)-1H-pyrrolizine-2-carboxamide

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Technology Process of (-)-(1S,2R,3S,7aR)-hexahydro-1-(hydroxymethyl)-3-(naphthalen-2-yl)-N-(phenylmethyl)-1H-pyrrolizine-2-carboxamide

There total 6 articles about (-)-(1S,2R,3S,7aR)-hexahydro-1-(hydroxymethyl)-3-(naphthalen-2-yl)-N-(phenylmethyl)-1H-pyrrolizine-2-carboxamide 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: 34.0%

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

: 935468-99-8
(-)-(1S,2R,3S,7aR)-hexahydro-1-(hydroxymethyl)-3-(naphthalen-2-yl)-N-(phenylmethyl)-1H-pyrrolizine-2-carboxamide

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at 0 ℃; for 2h;
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

: 935468-99-8
(-)-(1S,2R,3S,7aR)-hexahydro-1-(hydroxymethyl)-3-(naphthalen-2-yl)-N-(phenylmethyl)-1H-pyrrolizine-2-carboxamide

Guidance literature:: Multi-step reaction with 4 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

4.1: 34 percent / DIBAL-H / tetrahydrofuran; toluene / 2 h / 0 °C

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

Reference yield:

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

: 935468-99-8
(-)-(1S,2R,3S,7aR)-hexahydro-1-(hydroxymethyl)-3-(naphthalen-2-yl)-N-(phenylmethyl)-1H-pyrrolizine-2-carboxamide

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 83 percent / SOCl₂ / 15 h / 20 °C

2.1: 34 percent / DIBAL-H / tetrahydrofuran; toluene / 2 h / 0 °C

With sodium hydroxide; diisobutylaluminium hydride; In tetrahydrofuran; water; toluene;
DOI:10.1002/hlca.200790028