(-)-methyl (2S,3S,4R)-1-(tert-butoxycarbonyl)-2-(hydroxymethyl)-4-isopropenyl-pyrrolidine-3-acetate

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Chemical Name:(-)-methyl (2S,3S,4R)-1-(tert-butoxycarbonyl)-2-(hydroxymethyl)-4-isopropenyl-pyrrolidine-3-acetate
CAS No.:131305-02-7
Molecular Formula:C₁₆H₂₇NO₅
Molecular Weight:313.394
Hs Code.:

Synonyms:(-)-methyl (2S,3S,4R)-1-(tert-butoxycarbonyl)-2-(hydroxymethyl)-4-isopropenyl-pyrrolidine-3-acetate

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Chemical Property of (-)-methyl (2S,3S,4R)-1-(tert-butoxycarbonyl)-2-(hydroxymethyl)-4-isopropenyl-pyrrolidine-3-acetate

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Technology Process of (-)-methyl (2S,3S,4R)-1-(tert-butoxycarbonyl)-2-(hydroxymethyl)-4-isopropenyl-pyrrolidine-3-acetate

There total 1 articles about (-)-methyl (2S,3S,4R)-1-(tert-butoxycarbonyl)-2-(hydroxymethyl)-4-isopropenyl-pyrrolidine-3-acetate 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:

: 17342-08-4
(S)-Pyroglutaminol

: 131305-02-7
(-)-methyl (2S,3S,4R)-1-(tert-butoxycarbonyl)-2-(hydroxymethyl)-4-isopropenyl-pyrrolidine-3-acetate

Guidance literature:: Multi-step reaction with 16 steps

1.1: 99 percent / imidazole / dimethylformamide / 24 h / 20 °C

2.1: LiHMDS / tetrahydrofuran; hexane / 1 h / -20 °C

2.2: 98 percent / tetrahydrofuran; hexane / -20 - 20 °C

3.1: LiHMDS / tetrahydrofuran; hexane / 2 h

3.2: 85 percent / tetrahydrofuran; hexane / -78 - 20 °C

4.1: 75 percent / hydrogen peroxide / ethyl acetate / 0 - 20 °C

5.1: magnesium / tetrahydrofuran

5.2: CuBr*Me₂S / tetrahydrofuran / 0.17 h / -78 °C

5.3: 71 percent / trimethylsilyl chloride / tetrahydrofuran / 0.17 h / -78 °C

6.1: 90 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / 0.17 h

7.1: 95 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 24 h / 20 °C

8.1: 90 percent / DiBAl-H / tetrahydrofuran; hexane / 2 h / -78 °C

9.1: 50 percent / HCl / acetone; H₂O / 6 h / 20 °C

10.1: 70 percent / quinolinium camphorsulfonate / toluene / 0.33 h / 80 °C

11.1: 55 percent / SmI₂; HMPA / tetrahydrofuran; 2-methyl-propan-2-ol / 0.25 h / 20 °C

12.1: 72 percent / POCl₃; pyridine / 2 h / 0 °C

13.1: RuO₂*2H₂O; NaIO₄ / acetonitrile; CCl₄ / 4 h / 20 °C

14.1: K₂CO₃ / dimethylformamide / 2 h / 20 °C

15.1: 51 mg / TiCl₄; Zn / tetrahydrofuran / 24 h / 20 °C

16.1: 30 percent / HF / tetrahydrofuran / 0.33 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; ruthenium(IV) oxide; sodium periodate; samarium diiodide; quinolinium camphor-10-sulfonate; hydrogen fluoride; dihydrogen peroxide; titanium tetrachloride; sodium naphthalenide; diisobutylaluminium hydride; potassium carbonate; magnesium; triethylamine; lithium hexamethyldisilazane; zinc; trichlorophosphate; In tetrahydrofuran; tetrachloromethane; 1,2-dimethoxyethane; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; 1.1: Etherification / 2.1: Tosylation / 2.2: Tosylation / 3.1: Metallation / 3.2: phenylselenylation / 4.1: Oxidation / 5.1: Alkylation / 5.2: Alkylation / 5.3: Alkylation / 6.1: desulfonation / 7.1: tert-butoxycarbonylation / 8.1: Reduction / 9.1: Hydrolysis / 10.1: Dehydration / 11.1: Cyclization / 12.1: Dehydration / 13.1: Oxidation / 14.1: Methylation / 15.1: methylenation / 16.1: Hydrolysis;
DOI:10.1016/S0040-4020(99)00284-7

Reference yield:

: 131305-02-7
(-)-methyl (2S,3S,4R)-1-(tert-butoxycarbonyl)-2-(hydroxymethyl)-4-isopropenyl-pyrrolidine-3-acetate

: 487-79-6
(-)-kainic acid

Guidance literature:: Multi-step reaction with 4 steps

1: CrO₃, H₂SO₄ / acetone / 1 h / 0 °C

2: 9 mg / diethyl ether

3: KOH / tetrahydrofuran / 12 h / Ambient temperature

4: 4.5 mg / trifluoroacetic acid / CH₂Cl₂ / 12 h

With chromium(VI) oxide; potassium hydroxide; sulfuric acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;
DOI:10.1021/jo9604088

Reference yield:

: 131305-02-7,131305-03-8,139407-07-1,139407-15-1
1-tert-butoxycarbonyl-2-hydroxymethyl-4-isopropenyl-3-<(methoxycarbonyl)methyl>pyrrolidine

: 487-79-6,4071-39-0,59905-23-6,62137-25-1,69684-81-7,73209-05-9,88199-98-8,92219-21-1,132341-34-5,132341-35-6
(+/-)-α-kainic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 1) pyridinium dichromate / 1) DMF, 40 deg C, overnight, 2) ether, rt, 30 min

2: 99 percent / 1N NaOH / methanol / 2 h / Ambient temperature

3: 55 percent / trifluoroacetic acid / 0.67 h / Ambient temperature

With sodium hydroxide; dipyridinium dichromate; trifluoroacetic acid; In methanol;