(2R,4S)-1-allyloxycarbonyl-2-(2-aminoethyl)-4-(triphenylmethylthio)pyrrolidine

Base Information

Chemical Name:(2R,4S)-1-allyloxycarbonyl-2-(2-aminoethyl)-4-(triphenylmethylthio)pyrrolidine
CAS No.:156442-26-1
Molecular Formula:C₂₉H₃₂N₂O₂S
Molecular Weight:472.651
Hs Code.:

Synonyms:(2R,4S)-1-allyloxycarbonyl-2-(2-aminoethyl)-4-(triphenylmethylthio)pyrrolidine

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Chemical Property of (2R,4S)-1-allyloxycarbonyl-2-(2-aminoethyl)-4-(triphenylmethylthio)pyrrolidine

Chemical Property:

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Technology Process of (2R,4S)-1-allyloxycarbonyl-2-(2-aminoethyl)-4-(triphenylmethylthio)pyrrolidine

There total 12 articles about (2R,4S)-1-allyloxycarbonyl-2-(2-aminoethyl)-4-(triphenylmethylthio)pyrrolidine 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: 94.0%

: 156442-25-0
(2R,4S)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-(triphenylmethylthio)pyrrolidine

: 156442-26-1
(2R,4S)-1-allyloxycarbonyl-2-(2-aminoethyl)-4-(triphenylmethylthio)pyrrolidine

Guidance literature:: With triphenylphosphine; In pyridine; at 20 ℃; for 1h;
DOI:10.1016/S0968-0896(99)00085-1

Reference yield:

: 154343-02-9
(2S,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]-oxy}-1-benzyl-2-hydroxy-methyl-pyrrolidin

: 156442-26-1
(2R,4S)-1-allyloxycarbonyl-2-(2-aminoethyl)-4-(triphenylmethylthio)pyrrolidine

Guidance literature:: Multi-step reaction with 12 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.17 h / -50 - 20 °C

2.1: t-BuOK / tetrahydrofuran / 2 h / 20 °C

2.2: 50.4 percent / tetrahydrofuran / 1 h / 0 - 5 °C

3.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

3.2: 82.3 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

4.1: hydrogen / Pd/C / cyclopentane / 3 h / 20 °C / 760 Torr

5.1: 18.52 g / NaOH / tetrahydrofuran; H₂O / 0.5 h / 0 - 10 °C / pH 8 - 10

6.1: 75.6 percent / Et₃N / CH₂Cl₂ / 0 °C

7.1: 92 percent / NH₄Cl; NaN₃ / dimethylformamide / 3 h / 70 °C

8.1: 100 percent / conc. HCl / methanol / 0 - 5 °C

9.1: Et₃N / CH₂Cl₂ / 0 °C

10.1: 14.68 g / acetonitrile / 80 - 90 °C

11.1: NaOMe / tetrahydrofuran; methanol / 1 h / 0 °C

11.2: 67 percent / tetrahydrofuran; methanol / 5 h / 0 °C

12.1: 94 percent / Ph₃P / pyridine / 1 h / 20 °C

With hydrogenchloride; sodium hydroxide; sodium azide; oxalyl dichloride; potassium tert-butylate; hydrogen; sodium methylate; ammonium chloride; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; Cyclopentane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Swern oxidation / 2.1: Dehydrochlorination / 2.2: Wittig reaction / 3.1: hydroboration / 3.2: Oxidation / 4.1: Hydrogenolysis / 5.1: Acylation / 6.1: mesylation / 7.1: Substitution / 8.1: Hydrolysis / 9.1: mesylation / 10.1: Esterification / 11.1: Deacetylation / 11.2: Alkylation / 12.1: Reduction;
DOI:10.1016/S0968-0896(99)00085-1

Reference yield:

: 156440-98-1
(2S,4R)-N-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine-2-carbaldehyde

: 156442-26-1
(2R,4S)-1-allyloxycarbonyl-2-(2-aminoethyl)-4-(triphenylmethylthio)pyrrolidine

Guidance literature:: Multi-step reaction with 11 steps

1.1: t-BuOK / tetrahydrofuran / 2 h / 20 °C

1.2: 50.4 percent / tetrahydrofuran / 1 h / 0 - 5 °C

2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

2.2: 82.3 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

3.1: hydrogen / Pd/C / cyclopentane / 3 h / 20 °C / 760 Torr

4.1: 18.52 g / NaOH / tetrahydrofuran; H₂O / 0.5 h / 0 - 10 °C / pH 8 - 10

5.1: 75.6 percent / Et₃N / CH₂Cl₂ / 0 °C

6.1: 92 percent / NH₄Cl; NaN₃ / dimethylformamide / 3 h / 70 °C

7.1: 100 percent / conc. HCl / methanol / 0 - 5 °C

8.1: Et₃N / CH₂Cl₂ / 0 °C

9.1: 14.68 g / acetonitrile / 80 - 90 °C

10.1: NaOMe / tetrahydrofuran; methanol / 1 h / 0 °C

10.2: 67 percent / tetrahydrofuran; methanol / 5 h / 0 °C

11.1: 94 percent / Ph₃P / pyridine / 1 h / 20 °C

With hydrogenchloride; sodium hydroxide; sodium azide; potassium tert-butylate; hydrogen; sodium methylate; ammonium chloride; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; Cyclopentane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Dehydrochlorination / 1.2: Wittig reaction / 2.1: hydroboration / 2.2: Oxidation / 3.1: Hydrogenolysis / 4.1: Acylation / 5.1: mesylation / 6.1: Substitution / 7.1: Hydrolysis / 8.1: mesylation / 9.1: Esterification / 10.1: Deacetylation / 10.2: Alkylation / 11.1: Reduction;
DOI:10.1016/S0968-0896(99)00085-1