1-Piperidinecarboxylic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-phenyl-, 1,1-dimethylethyl ester, (2S,3S)-

Base Information

• Chemical Name: 1-Piperidinecarboxylic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-phenyl-, 1,1-dimethylethyl ester, (2S,3S)-
• CAS No.: 757195-59-8
• Molecular Formula: C22H37NO3Si
• Molecular Weight: 391.626
• Mol file: 757195-59-8.mol

Synonyms:

Chemical Property of 1-Piperidinecarboxylic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-phenyl-, 1,1-dimethylethyl ester, (2S,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Piperidinecarboxylic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-phenyl-, 1,1-dimethylethyl ester, (2S,3S)-

There total 20 articles about 1-Piperidinecarboxylic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-phenyl-, 1,1-dimethylethyl ester, (2S,3S)- 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: 99.0%

tert-butyl (1S,2S)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-1-phenylpentylcarbamate (757195-54-3) → (2S,3S)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-phenylpiperidine-1-carboxylate (757195-59-8)

Guidance literature:

tert-butyl (1S,2S)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-1-phenylpentylcarbamate; With methanesulfonyl chloride; triethylamine; In dichloromethane; at -78 ℃; for 3h;

With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol0528235

Reference yield: 95.0%

(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-piperidine (944324-86-1) + di-tert-butyl dicarbonate (24424-99-5) → (2S,3S)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-phenylpiperidine-1-carboxylate (757195-59-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tetasy.2007.04.006

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (2S,3S)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-phenylpiperidine-1-carboxylate (757195-59-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 89 percent / (2S,3S)-(-)-diisopropyl tartrate; activated molecular sieves 4 Angstroem; TBHP / Ti(Oi-Pr)4 / CH₂Cl₂ / 3.5 h / -20 °C

2: 98 percent / NaN₃; NH₄Cl; H₂O / methanol / 5 h / 65 °C

3: pyridine / CH₂Cl₂ / 0 - 20 °C

4: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 20 °C

5: 5.08 g / K₂CO₃ / methanol / 20 °C

6: 65 percent / TiCl₄ / CH₂Cl₂ / 1.5 h / -78 °C

7: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

8: 2,6-lutidine; OsO₄; NaIO₄ / dioxane; H₂O; toluene / 3 h / 25 °C

9: triphenylphosphine / tetrahydrofuran / 16 h / 20 °C

10: 0.86 g / NaBH₄ / methanol; tetrahydrofuran / 0.5 h / 0 °C

11: 95 percent / triethylamine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium azide; 4 A molecular sieve; water; titanium tetrachloride; potassium carbonate; ammonium chloride; triethylamine; triphenylphosphine; titanium(IV) isopropylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; toluene; 1: Sharpless asymmetric epoxidation;

DOI:10.1016/j.tetasy.2007.04.006

upstream raw materials:

tert-butyl (1S,2S)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-1-phenylpentylcarbamate

(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-piperidine

di-tert-butyl dicarbonate

(1S,2S)-1-azido-1-phenyl-hex-5-en-2-ol

Downstream raw materials:

tert-butyl (2S,3S)-3-hydroxy-2-phenylpiperidine-1-carboxylate

L 733060

(2S,3S)-1-(tert-butyloxycarbonyl)-2-phenyl-3-[(3,5)-bis(trifluoromethyl)benzyloxy]piperidine