2,2,2-Trifluoro-N-{(1S,2S)-2-[(S)-1-(2-hydroxy-ethyl)-1-methyl-but-3-enyloxy]-1-methyl-2-phenyl-ethyl}-acetamide

Base Information

Chemical Name:2,2,2-Trifluoro-N-{(1S,2S)-2-[(S)-1-(2-hydroxy-ethyl)-1-methyl-but-3-enyloxy]-1-methyl-2-phenyl-ethyl}-acetamide
CAS No.:247256-66-2
Molecular Formula:C₁₈H₂₄F₃NO₃
Molecular Weight:359.389
Hs Code.:

Synonyms:2,2,2-Trifluoro-N-{(1S,2S)-2-[(S)-1-(2-hydroxy-ethyl)-1-methyl-but-3-enyloxy]-1-methyl-2-phenyl-ethyl}-acetamide

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Chemical Property of 2,2,2-Trifluoro-N-{(1S,2S)-2-[(S)-1-(2-hydroxy-ethyl)-1-methyl-but-3-enyloxy]-1-methyl-2-phenyl-ethyl}-acetamide

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Technology Process of 2,2,2-Trifluoro-N-{(1S,2S)-2-[(S)-1-(2-hydroxy-ethyl)-1-methyl-but-3-enyloxy]-1-methyl-2-phenyl-ethyl}-acetamide

There total 2 articles about 2,2,2-Trifluoro-N-{(1S,2S)-2-[(S)-1-(2-hydroxy-ethyl)-1-methyl-but-3-enyloxy]-1-methyl-2-phenyl-ethyl}-acetamide 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: 73.0%

: 214959-70-3
(3S,1'S,2'S)-1-tert-Butyldiphenylsiloxy-3-methyl-3-(1'-phenyl-2'-trifluoroacetamido-1'-propoxy)hex-5-en

: 247256-66-2
2,2,2-Trifluoro-N-{(1S,2S)-2-[(S)-1-(2-hydroxy-ethyl)-1-methyl-but-3-enyloxy]-1-methyl-2-phenyl-ethyl}-acetamide

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 20 ℃;
DOI:10.1002/1521-3773(20010302)40:5<901::AID-ANIE901>3.0.CO;2-F

Reference yield:

: 183378-05-4
trimethylsilyl ether of (1S,2S)-N-trifluoroacetamidonorpseudoephedrine

: 247256-66-2
2,2,2-Trifluoro-N-{(1S,2S)-2-[(S)-1-(2-hydroxy-ethyl)-1-methyl-but-3-enyloxy]-1-methyl-2-phenyl-ethyl}-acetamide

Guidance literature:: Multi-step reaction with 2 steps

1: TfOH / CH₂Cl₂ / 17 h / -78 °C

2: 73 percent / aq. HF / acetonitrile / 20 °C

With trifluorormethanesulfonic acid; hydrogen fluoride; In dichloromethane; acetonitrile;
DOI:10.1002/1521-3773(20010302)40:5<901::AID-ANIE901>3.0.CO;2-F

Reference yield:

: 247256-66-2
2,2,2-Trifluoro-N-{(1S,2S)-2-[(S)-1-(2-hydroxy-ethyl)-1-methyl-but-3-enyloxy]-1-methyl-2-phenyl-ethyl}-acetamide

: (3E,9E)-(5R,13S,14R)-5-(4-Methoxy-benzyloxy)-5,9,13,14-tetramethyl-oxacyclotetradeca-3,9-diene-2,8-dione

Guidance literature:: Multi-step reaction with 17 steps

1.1: 90 percent / Li; NH₃ / tetrahydrofuran / -78 °C

2.1: 99 percent / DMAP; imidazole / dimethylformamide / 20 °C

3.1: TfOH / diethyl ether / 0 °C

4.1: TBAF*3H₂O / tetrahydrofuran / 50 °C

5.1: 90 percent / I₂; imidazole; PPh₃ / CH₂Cl₂ / 20 °C

6.1: sec-BuLi / diethyl ether / 0.17 h / -78 °C

6.2: 68 percent / diethyl ether / 0.17 h

7.1: 90 percent / imidazole; DMAP / dimethylformamide / 50 °C

8.1: 9-BBN / tetrahydrofuran / 50 °C

8.2: 78 percent / aq. H₂O₂; NaOH

9.1: o-iodoxybenzoic acid; 1-hydroxy-1,2-benziodoxol-3(1H)-one-1-oxide / tetrahydrofuran; dimethylformamide / 20 °C

10.1: NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s) / 20 °C

11.1: aq. HF; pyridine / acetonitrile / 20 °C

12.1: iPr₂NEt / tetrahydrofuran / 0 °C

13.1: DMAP / tetrahydrofuran; toluene / 20 °C

14.1: LHMDS / tetrahydrofuran / -78 °C

15.1: Pd(OAc)2; MS 3A / acetonitrile / 20 °C

16.1: 72 percent / HF*pyridine; pyridine / 60 °C

17.1: 90 percent / o-iodoxybenzoic acid; 1-hydroxy-1,2-benziodoxol-3(1H)-one-1-oxide / tetrahydrofuran; dimethylformamide / 20 °C

With pyridine; 1H-imidazole; dmap; palladium diacetate; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; trifluorormethanesulfonic acid; hydrogen fluoride; tetrabutyl ammonium fluoride; ammonia; iodine; sec.-butyllithium; lithium; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 13.1: Yamaguchi lactonization;
DOI:10.1002/1521-3773(20010302)40:5<901::AID-ANIE901>3.0.CO;2-F