(3'S,4'R)-[(1R)-2-hydroxy-1-phenylethyl]-4'-amino-3',4'-dihydrospiro[piperidine-2,3'(2'H)-benzopyran]

Base Information

Chemical Name:(3'S,4'R)-[(1R)-2-hydroxy-1-phenylethyl]-4'-amino-3',4'-dihydrospiro[piperidine-2,3'(2'H)-benzopyran]
CAS No.:500131-70-4
Molecular Formula:C₂₁H₂₆N₂O₂
Molecular Weight:338.45
Hs Code.:

Synonyms:(3'S,4'R)-[(1R)-2-hydroxy-1-phenylethyl]-4'-amino-3',4'-dihydrospiro[piperidine-2,3'(2'H)-benzopyran]

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Chemical Property of (3'S,4'R)-[(1R)-2-hydroxy-1-phenylethyl]-4'-amino-3',4'-dihydrospiro[piperidine-2,3'(2'H)-benzopyran]

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Technology Process of (3'S,4'R)-[(1R)-2-hydroxy-1-phenylethyl]-4'-amino-3',4'-dihydrospiro[piperidine-2,3'(2'H)-benzopyran]

There total 5 articles about (3'S,4'R)-[(1R)-2-hydroxy-1-phenylethyl]-4'-amino-3',4'-dihydrospiro[piperidine-2,3'(2'H)-benzopyran] 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: 99.0%

: 500131-68-0
(3S,8aR,14bS)-3-phenyl-2,3,5,6,7,8-hexahydro-14bH-chromeno[4,3-b]pyrido[2,1-c][1,4]oxazin-14b-amine

: 500131-70-4
(3'S,4'R)-[(1R)-2-hydroxy-1-phenylethyl]-4'-amino-3',4'-dihydrospiro[piperidine-2,3'(2'H)-benzopyran]

Guidance literature:: (3S,8aR,14bS)-3-phenyl-2,3,5,6,7,8-hexahydro-14bH-chromeno[4,3-b]pyrido[2,1-c][1,4]oxazin-14b-amine; With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; at 0 ℃; for 3h;

With water; for 18h; Further stages.;
DOI:10.1021/jo026228h

Reference yield:

: 54257-94-2
1-Bromo-2-chloro-methoxybenzene

: 500131-70-4
(3'S,4'R)-[(1R)-2-hydroxy-1-phenylethyl]-4'-amino-3',4'-dihydrospiro[piperidine-2,3'(2'H)-benzopyran]

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 62 percent / HMPA / tetrahydrofuran; hexane / 3 h

2.1: 91 percent / n-BuLi / diethyl ether; hexane / 2 h / -78 °C

3.1: 80 percent / NaBH₃CN; 1 N aq. HCl / tetrahydrofuran / 4 h / pH 3 / Heating

4.1: LiAlH₄; AlCl₃ / tetrahydrofuran / 3 h / 0 °C

4.2: 99 percent / 10percent NaOH; H₂O / 18 h

With hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; sodium cyanoborohydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1021/jo026228h

Reference yield:

: 88056-92-2
(-)-2-cyano-6-phenyloxazolopiperidine

: 500131-70-4
(3'S,4'R)-[(1R)-2-hydroxy-1-phenylethyl]-4'-amino-3',4'-dihydrospiro[piperidine-2,3'(2'H)-benzopyran]

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 62 percent / HMPA / tetrahydrofuran; hexane / 3 h

2.1: 91 percent / n-BuLi / diethyl ether; hexane / 2 h / -78 °C

3.1: 80 percent / NaBH₃CN; 1 N aq. HCl / tetrahydrofuran / 4 h / pH 3 / Heating

4.1: LiAlH₄; AlCl₃ / tetrahydrofuran / 3 h / 0 °C

4.2: 99 percent / 10percent NaOH; H₂O / 18 h

With hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; sodium cyanoborohydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1021/jo026228h