3-(R)-but-2-enyl-2-oxo-5-(R),6-(S)-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

Base Information

Chemical Name:3-(R)-but-2-enyl-2-oxo-5-(R),6-(S)-diphenyl-morpholine-4-carboxylic acid tert-butyl ester
CAS No.:732278-75-0
Molecular Formula:C₂₅H₂₉NO₄
Molecular Weight:407.51
Hs Code.:

Synonyms:3-(R)-but-2-enyl-2-oxo-5-(R),6-(S)-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

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Chemical Property of 3-(R)-but-2-enyl-2-oxo-5-(R),6-(S)-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

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Technology Process of 3-(R)-but-2-enyl-2-oxo-5-(R),6-(S)-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

There total 2 articles about 3-(R)-but-2-enyl-2-oxo-5-(R),6-(S)-diphenyl-morpholine-4-carboxylic acid tert-butyl ester 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: 92.0%

: 38169-04-9
(E)-crotyl iodide

: 112741-50-1,173397-90-5
(2S,3R)-tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate

: 732278-75-0
3-(R)-but-2-enyl-2-oxo-5-(R),6-(S)-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; hexane; toluene; for 0.5h;
DOI:10.1016/j.tet.2006.02.044

Reference yield: 64.0%

: 4894-61-5
trans-but-2-enyl chloride

: 112741-50-1,173397-90-5
(2S,3R)-tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate

: 732278-75-0
3-(R)-but-2-enyl-2-oxo-5-(R),6-(S)-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1016/j.tet.2006.02.044

Reference yield:

: 732278-75-0
3-(R)-but-2-enyl-2-oxo-5-(R),6-(S)-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

: (2S,3R,4S,6R)-6-Hydroxymethyl-2-[(4-methoxy-benzylamino)-methyl]-3-methyl-piperidin-4-ol

Guidance literature:: Multi-step reaction with 8 steps

1: lithium; ammonia / tetrahydrofuran; ethanol / 0.5 h / -33 °C

2: acetyl chloride / 0 - 20 °C

3: 487 mg / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

4: 63 percent / (i-Pr)2NEt / acetonitrile / 4 h

5: 84 percent / mCPBA; Na₂HPO₄ / CH₂Cl₂ / 0.5 h / -78 °C

6: toluene / 2.5 h / 200 °C

7: 87 percent / DIBAL-H / CH₂Cl₂; toluene / -78 - 20 °C

8: H₂ / Pd/C / ethyl acetate / 12 h / 760 Torr

With disodium hydrogenphosphate; lithium aluminium tetrahydride; ammonia; hydrogen; lithium; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; toluene; acetonitrile;
DOI:10.1016/j.tet.2006.02.044