1-((3R,4S)-7-Benzyloxy-4-hydroxy-chroman-3-yl)-4-(4-fluoro-phenyl)-piperidin-4-ol

Base Information

Chemical Name:1-((3R,4S)-7-Benzyloxy-4-hydroxy-chroman-3-yl)-4-(4-fluoro-phenyl)-piperidin-4-ol
CAS No.:171866-33-4
Molecular Formula:C₂₇H₂₈FNO₄
Molecular Weight:449.522
Hs Code.:

Synonyms:1-((3R,4S)-7-Benzyloxy-4-hydroxy-chroman-3-yl)-4-(4-fluoro-phenyl)-piperidin-4-ol

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Chemical Property of 1-((3R,4S)-7-Benzyloxy-4-hydroxy-chroman-3-yl)-4-(4-fluoro-phenyl)-piperidin-4-ol

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Technology Process of 1-((3R,4S)-7-Benzyloxy-4-hydroxy-chroman-3-yl)-4-(4-fluoro-phenyl)-piperidin-4-ol

There total 7 articles about 1-((3R,4S)-7-Benzyloxy-4-hydroxy-chroman-3-yl)-4-(4-fluoro-phenyl)-piperidin-4-ol 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: 77.0%

: (R)-Pyrrolidine-1,2-dicarboxylic acid 2-{(3R,4S)-7-benzyloxy-3-[4-(4-fluoro-phenyl)-4-hydroxy-piperidin-1-yl]-chroman-4-yl} ester 1-tert-butyl ester

: 171866-33-4
1-((3R,4S)-7-Benzyloxy-4-hydroxy-chroman-3-yl)-4-(4-fluoro-phenyl)-piperidin-4-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.5h; Ambient temperature;
DOI:10.1021/jm9707986

Reference yield:

: 76240-27-2
7-hydroxy-2,3-dihydro-4H-chromen-4-one

: 171866-33-4
1-((3R,4S)-7-Benzyloxy-4-hydroxy-chroman-3-yl)-4-(4-fluoro-phenyl)-piperidin-4-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / K₂CO₃ / acetone / 6 h / Heating

2: 41 percent / Br₂ / ethyl acetate / 2 h

3: 93 percent / Et₃N / acetonitrile / 16 h

4: 90 percent / NaBH₄ / tetrahydrofuran; ethanol / 40 h

5: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide*HCl, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.3 h / Heating

6: 77 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

With dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; bromine; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; acetone; acetonitrile;
DOI:10.1021/jm9707986

Reference yield:

: 31042-20-3
7-(benzyloxy)chroman-4-one

: 171866-33-4
1-((3R,4S)-7-Benzyloxy-4-hydroxy-chroman-3-yl)-4-(4-fluoro-phenyl)-piperidin-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 41 percent / Br₂ / ethyl acetate / 2 h

2: 93 percent / Et₃N / acetonitrile / 16 h

3: 90 percent / NaBH₄ / tetrahydrofuran; ethanol / 40 h

4: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide*HCl, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.3 h / Heating

5: 77 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

With dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; bromine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jm9707986