(3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane

Base Information

• Chemical Name: (3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane
• CAS No.: 1208008-34-7
• Molecular Formula: C₁₁H₁₉NO₃
• Molecular Weight: 213.277
• Mol file: 1208008-34-7.mol

Synonyms:(3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane

Chemical Property of (3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane

Chemical Property:

Purity/Quality:

98%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane

There total 12 articles about (3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane 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%

(3S)-tert-butyl 3-(tert-butyldiphenylsiloxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate (1208008-33-6) → (3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane (1208008-34-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4.75h;

Reference yield: 65.0%

C11H17NO4 (1419390-03-6) → (3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane (1208008-34-7)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane (1208008-34-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap; triethylamine / dichloromethane / 20 °C

2.1: dmap; triethylamine / dichloromethane / 18.16 h / 24 °C

3.1: lithium triethylborohydride / toluene; tetrahydrofuran / 1.08 h / -50 - -45 °C

3.2: 14.42 h / -50 - 20 °C

3.3: 0.08 h / Cooling with ice/water

4.1: diethylzinc / toluene / 0.25 h / -30 °C

4.2: 19.66 h / -25 - -21 °C

4.3: 0.33 h / -25 - 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4.83 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; diethylzinc; lithium triethylborohydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

upstream raw materials:

(3S)-tert-butyl 3-(tert-butyldiphenylsiloxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

(5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one

(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

(S)-Pyroglutaminol

Downstream raw materials:

(1R,3S,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

(1R,3S,5R)-tert-butyl 3-(5-(4-bromophenyl)-1H-imidazol-2-yl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

3-hydroxymethyl-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester