tert-Butyl ((1R,5S,6s)-3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamate

Base Information

• Chemical Name: tert-Butyl ((1R,5S,6s)-3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamate
• CAS No.: 185559-52-8
• Molecular Formula: C₁₇H₂₄N₂O₂
• Molecular Weight: 288.39
• DSSTox Substance ID: DTXSID80453171,DTXSID901113710
• Nikkaji Number: J788.958E
• Wikidata: Q82274225
• Mol file: 185559-52-8.mol

Synonyms:185559-52-8;tert-Butyl ((1R,5S,6s)-3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamate;151860-18-3;tert-butyl (1R,5S,6s)-3-benzyl-3-aza-bicyclo[3.1.0]hexan-6-ylcarbamate;TERT-BUTYL N-[(1R,5S)-3-BENZYL-3-AZABICYCLO[3.1.0]HEXAN-6-YL]CARBAMATE;Carbamic acid, N-[(1alpha,5alpha,6alpha)-3-(phenylmethyl)-3-azabicyclo[3.1.0]hex-6-yl]-, 1,1-dimethylethyl ester;CarbaMic acid, [3-(phenylMethyl)-3-azabicyclo[3.1.0]hex-6-yl]-, 1,1-diMethylethyl ester, [1R-(1a,5a,;DTXSID80453171;JYIFMNXUMIYQHE-YIONKMFJSA-N;DTXSID901113710;AKOS016012345;AKOS037651918;tert-Butyl((1R,5S,6s)-3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamate;SB48322;BP-13385;A12638;tert-butyl(1S,5R)-3-benzyl-3-aza-bicyclo[3.1.0]hexan-6-ylcarbamate;N-[(1alpha,5alpha)-3-Benzyl-3-azabicyclo[3.1.0]hexan-6alpha-yl]carbamic acid tert-butyl ester

Chemical Property of tert-Butyl ((1R,5S,6s)-3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamate

Chemical Property:

• PSA: 45.06000
• LogP: 2.78380
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 288.183778013
• Heavy Atom Count: 21
• Complexity: 373

Purity/Quality:

≥99% ^*data from raw suppliers

tert-Butyl (1R,5S,6S)-3-benzyl-3-azabicyclo[3.1.0]hexan-6-ylcarbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1C2C1CN(C2)CC3=CC=CC=C3
• Isomeric SMILES: CC(C)(C)OC(=O)NC1[C@H]2[C@@H]1CN(C2)CC3=CC=CC=C3

Technology Process of tert-Butyl ((1R,5S,6s)-3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamate

There total 4 articles about tert-Butyl ((1R,5S,6s)-3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamate 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: 90.0%

di-tert-butyl dicarbonate (24424-99-5) + (1α,5α,6α)-3-N-benzyl-6-amino-3-aza-bicyclo[3.1.0]hexane (151860-17-2) → (1α,5α,6α)-3-N-benzyl-6-[t-butoxycarbonylamino]-3-aza-bicyclo[3.1.0]hexane (185559-52-8,151860-18-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 10 - 20 ℃; for 4.16667h;

Reference yield:

1-benzyl-1H-pyrrole-2,5-dione (1631-26-1) → (1α,5α,6α)-3-N-benzyl-6-[t-butoxycarbonylamino]-3-aza-bicyclo[3.1.0]hexane (185559-52-8,151860-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 43 percent / tetrabutylammonium 2,6-di-tert-butylphenoxide; 4 Angstroem molecular sieves / toluene / 1 h / -19 °C

2: 97 percent / NaBH₄; BF₃*THF / tetrahydrofuran / 3 h / 40 °C

3: H₂; H₂O / 5percent Pt/C / methanol / 24 h / 50 °C / 2660.18 Torr

4: Na₂CO₃; aq. NaOH / ethyl acetate / 3 h / 30 °C

With sodium hydroxide; sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex; tetrabutylammonium 2,6-di-tert-butylphenoxide; 4 A molecular sieve; water; hydrogen; sodium carbonate; 5percent Pt/C; In tetrahydrofuran; methanol; ethyl acetate; toluene; 1: Cycloaddition / 2: Reduction / 3: Reduction / 4: Acylation;

DOI:10.1039/a910340f

Reference yield:

(1α,5α,6α)-3-N-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane (151860-16-1) → (1α,5α,6α)-3-N-benzyl-6-[t-butoxycarbonylamino]-3-aza-bicyclo[3.1.0]hexane (185559-52-8,151860-18-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂; H₂O / 5percent Pt/C / methanol / 24 h / 50 °C / 2660.18 Torr

2: Na₂CO₃; aq. NaOH / ethyl acetate / 3 h / 30 °C

With sodium hydroxide; water; hydrogen; sodium carbonate; 5percent Pt/C; In methanol; ethyl acetate; 1: Reduction / 2: Acylation;

DOI:10.1039/a910340f

upstream raw materials:

di-tert-butyl dicarbonate

(1α,5α,6α)-3-N-benzyl-6-amino-3-aza-bicyclo[3.1.0]hexane

1-benzyl-1H-pyrrole-2,5-dione

(1α,5α,6α)-3-N-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane

Downstream raw materials:

tert-butyl (1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate

trovafloxacin mesylate

(1α,5α,6α)-6-Amino-3-azabicyclo[3.1.0]hexane ditosylate salt

7-([1α,5α,6α]-6-tert-Butoxycarbonylamino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid,ethyl ester