(S)-2-{[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]-methyl-amino}-3-methyl-butyric acid benzyl ester

Base Information

• Chemical Name: (S)-2-{[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]-methyl-amino}-3-methyl-butyric acid benzyl ester
• CAS No.: 205385-92-8
• Molecular Formula: C₃₃H₄₈N₂O₅
• Molecular Weight: 552.755
• Mol file: 205385-92-8.mol

Synonyms:(S)-2-{[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]-methyl-amino}-3-methyl-butyric acid benzyl ester

Chemical Property of (S)-2-{[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]-methyl-amino}-3-methyl-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]-methyl-amino}-3-methyl-butyric acid benzyl ester

There total 17 articles about (S)-2-{[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]-methyl-amino}-3-methyl-butyric acid benzyl 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: 82.0%

[2-(5,5-Dimethyl-3-methylamino-5,6,7,8-tetrahydro-naphthalen-2-yl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester (205385-91-7) + benzyl D-2-trifluoromethylsulphonyloxy-3-methylbutanoate (155137-33-0) → (S)-2-{[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]-methyl-amino}-3-methyl-butyric acid benzyl ester (205385-92-8)

Guidance literature:

With 2,6-dimethylpyridine; In 1,2-dichloro-ethane; for 48h; Heating;

DOI:10.1021/jm970704s

Reference yield:

dihydro-5,5-dimethyl-2(3H)-furanone (3123-97-5) → (S)-2-{[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]-methyl-amino}-3-methyl-butyric acid benzyl ester (205385-92-8)

Guidance literature:

Multi-step reaction with 16 steps

1: 72 percent / AlCl₃ / 2.5 h / 90 - 100 °C

2: 65 percent / AlCl₃, Br₂ / CH₂Cl₂ / 0.5 h / 80 °C

3: 65 percent / CF₃COOH, triethylsilane / 8 h / 0 - 20 °C

4: 1.) n-BuLi / 1.) ether, hexane, RT, 40 min, 2.) ether, hexane, 0 def C, 20 min

5: NaBH₄ / methanol / 0.5 h / 0 °C

6: CHBr₃, Ph₃P / CH₂Cl₂ / 0.25 h / 0 °C

7: 32 percent / fuming HNO₃, AcOH, Ac₂O / 0.33 h / 0 °C

8: 97 percent / NaH / dimethylformamide / 2.5 h / Ambient temperature

9: conc. aq. HCl / acetic acid / 14 h / Heating

10: SOCl₂ / 20 h / Ambient temperature

11: CH₂Cl₂ / 18 h / Ambient temperature

12: LiBH₄ / tetrahydrofuran / 19 h / 0 - 20 °C

13: 92 percent / H₂ / 10percent Pd/C / ethanol / 6 h / 760 Torr / Ambient temperature

14: acetic anhydride / tetrahydrofuran / 2 h / 60 - 70 °C

15: BH₃ / tetrahydrofuran / 3 h / 0 °C

16: 82 percent / 2,6-lutidine / 1,2-dichloro-ethane / 48 h / Heating

With 2,6-dimethylpyridine; hydrogenchloride; triethylsilane; sodium tetrahydroborate; lithium borohydride; n-butyllithium; aluminium trichloride; thionyl chloride; Bromoform; borane; hydrogen; bromine; nitric acid; acetic anhydride; sodium hydride; acetic acid; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm970704s

Reference yield:

3,4-dihydro-4,4-dimethyl-1(2H)-naphthalenone (2979-69-3) → (S)-2-{[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]-methyl-amino}-3-methyl-butyric acid benzyl ester (205385-92-8)

Guidance literature:

Multi-step reaction with 15 steps

1: 65 percent / AlCl₃, Br₂ / CH₂Cl₂ / 0.5 h / 80 °C

2: 65 percent / CF₃COOH, triethylsilane / 8 h / 0 - 20 °C

3: 1.) n-BuLi / 1.) ether, hexane, RT, 40 min, 2.) ether, hexane, 0 def C, 20 min

4: NaBH₄ / methanol / 0.5 h / 0 °C

5: CHBr₃, Ph₃P / CH₂Cl₂ / 0.25 h / 0 °C

6: 32 percent / fuming HNO₃, AcOH, Ac₂O / 0.33 h / 0 °C

7: 97 percent / NaH / dimethylformamide / 2.5 h / Ambient temperature

8: conc. aq. HCl / acetic acid / 14 h / Heating

9: SOCl₂ / 20 h / Ambient temperature

10: CH₂Cl₂ / 18 h / Ambient temperature

11: LiBH₄ / tetrahydrofuran / 19 h / 0 - 20 °C

12: 92 percent / H₂ / 10percent Pd/C / ethanol / 6 h / 760 Torr / Ambient temperature

13: acetic anhydride / tetrahydrofuran / 2 h / 60 - 70 °C

14: BH₃ / tetrahydrofuran / 3 h / 0 °C

15: 82 percent / 2,6-lutidine / 1,2-dichloro-ethane / 48 h / Heating

With 2,6-dimethylpyridine; hydrogenchloride; triethylsilane; sodium tetrahydroborate; lithium borohydride; n-butyllithium; aluminium trichloride; thionyl chloride; Bromoform; borane; hydrogen; bromine; nitric acid; acetic anhydride; sodium hydride; acetic acid; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm970704s

upstream raw materials:

[2-(5,5-Dimethyl-3-methylamino-5,6,7,8-tetrahydro-naphthalen-2-yl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

benzyl D-2-trifluoromethylsulphonyloxy-3-methylbutanoate

dihydro-5,5-dimethyl-2(3H)-furanone

3,4-dihydro-4,4-dimethyl-1(2H)-naphthalenone