(+)-(3R,1′S,2'S)-N-(1'-hydroxy-1'-phenylpropan-2'-yl)-3-(furan-2-yl)-N-methylbutanamide

Base Information

Chemical Name:(+)-(3R,1′S,2'S)-N-(1'-hydroxy-1'-phenylpropan-2'-yl)-3-(furan-2-yl)-N-methylbutanamide
CAS No.:1417920-26-3
Molecular Formula:C₁₈H₂₃NO₃
Molecular Weight:301.386
Hs Code.:

Synonyms:(+)-(3R,1′S,2'S)-N-(1'-hydroxy-1'-phenylpropan-2'-yl)-3-(furan-2-yl)-N-methylbutanamide

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Chemical Property of (+)-(3R,1′S,2'S)-N-(1'-hydroxy-1'-phenylpropan-2'-yl)-3-(furan-2-yl)-N-methylbutanamide

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Technology Process of (+)-(3R,1′S,2'S)-N-(1'-hydroxy-1'-phenylpropan-2'-yl)-3-(furan-2-yl)-N-methylbutanamide

There total 2 articles about (+)-(3R,1′S,2'S)-N-(1'-hydroxy-1'-phenylpropan-2'-yl)-3-(furan-2-yl)-N-methylbutanamide 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: 54.0%

: 584-12-3
2-bromofuran

: N-crotonyl pseudoephedrine

: 1417920-26-3
(+)-(3R,1′S,2'S)-N-(1'-hydroxy-1'-phenylpropan-2'-yl)-3-(furan-2-yl)-N-methylbutanamide

Guidance literature:: 2-bromofuran; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 1h;

N-crotonyl pseudoephedrine; With lithium chloride; In tetrahydrofuran; at -78 ℃; Concentration; Reagent/catalyst; Temperature; diastereoselective reaction;
DOI:10.1021/jo302438k

Reference yield:

: 584-12-3
2-bromofuran

: N-crotonyl pseudoephedrine

: 1417920-26-3
(+)-(3R,1′S,2'S)-N-(1'-hydroxy-1'-phenylpropan-2'-yl)-3-(furan-2-yl)-N-methylbutanamide

: 1417920-29-6
C₁₈H₂₃NO₃

Guidance literature:: 2-bromofuran; With n-butyllithium; In toluene; at 0 ℃; for 1h;

N-crotonyl pseudoephedrine; With lithium chloride; In toluene; at -78 ℃; Overall yield = 56 %; diastereoselective reaction;
DOI:10.1021/jo302438k

Reference yield:

: 1417920-26-3
(+)-(3R,1′S,2'S)-N-(1'-hydroxy-1'-phenylpropan-2'-yl)-3-(furan-2-yl)-N-methylbutanamide

: 2938-98-9,70423-38-0,101978-85-2,22644-28-6
(R)-2-methylbutane-1,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1: n-butyllithium; borane-ammonia complex; diisopropylamine / tetrahydrofuran / 2 h / 0 °C

2: 1H-imidazole; dmap / tetrahydrofuran / 18 h / 20 °C

3: sodium periodate; rhodium(III) chloride hydrate / tetrachloromethane; acetonitrile; water / 1 h / 20 °C

4: borane-THF / tetrahydrofuran / 3.5 h / 20 °C

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C

With 1H-imidazole; dmap; sodium periodate; n-butyllithium; borane-ammonia complex; borane-THF; rhodium(III) chloride hydrate; tetrabutyl ammonium fluoride; diisopropylamine; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;
DOI:10.1021/jo302438k