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

Base Information

• Chemical Name: tert-butyl (1R,5S,6r)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate
• CAS No.: 134575-17-0
• Molecular Formula: C10H18N2O2
• Molecular Weight: 198.265
• European Community (EC) Number: 429-170-8,683-592-9
• DSSTox Substance ID: DTXSID40928678
• Nikkaji Number: J788.947J
• Wikidata: Q76416687
• Mol file: 134575-17-0.mol

Synonyms:134575-17-0;134677-60-4;tert-butyl (1R,5S,6r)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate;exo-6-(Boc-amino)-3-azabicyclo[3.1.0]hexane;TERT-BUTYL N-[(1S,5R)-3-AZABICYCLO[3.1.0]HEXAN-6-YL]CARBAMATE;tert-Butyl (1R,5S,6s)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate;tert-butyl N-[(1R,5S)-3-azabicyclo[3.1.0]hexan-6-yl]carbamate;tert-Butyl (1R,5S)-3-azabicyclo[3.1.0]hex-6-ylcarbamate;tert-butyl N-[exo-3-azabicyclo[3.1.0]hexan-6-yl]carbamate;CP-101537;tert-Butyl (1R,5S,6r)-rel-3-azabicyclo[3.1.0]hexan-6-ylcarbamate;N-(1alpha,5alpha,6alpha)-3-Alphazabicyclo[3.1.0]hex-6-yl-carbamic Acid 1,1-Dimethylethyl Ester;tert-Butyl (1R,5S,6s)-rel-3-azabicyclo[3.1.0]hexan-6-ylcarbamate;tert-butyl (1r,5s)-3-azabicyclo(3.1.0)hex-6-ylcarbamate;MFCD12198677;exo-6-(Boc-amino)-3-Aza-bicyclo[3.1.0]hexane;(3-Aza-bicyclo[3.1.0]hex-6-yl)-carbamicacidtert-butylester;SCHEMBL523501;SCHEMBL523528;CS-WAA0044;SCHEMBL9470001;SCHEMBL22830486;SCHEMBL22830489;DTXSID40928678;HMS3262I08;Tox21_500763;tert-butyl N-[(1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-yl]carbamate;AKOS006345329;AKOS025311339;CCG-222067;CS-W004230;CS-W022963;PB35954;SB10057;SB10391;NCGC00261448-01;AM806031;AM806032;AS-33410;CS-13091;EN300-268774;CP-101537, >=98% (HPLC);A925530;W-205445;Z1201626435;tert-butyl N-[(1R,5S,6S)-3-azabicyclo[3.1.0]hexan-6-;tert-butyl (1R,5S,6s)-3-azabicyclo[3.1.0]hex-6-ylcarbamate;TERT-BUTYL -3-AZABICYCLO[3.1.0]HEXAN-6-YLCARBAMATE;tert-butyl N-[endo-3-azabicyclo[3.1.0]hexan-6-yl]carbamate;tert-butyl ((1R,5S,6r)-3-azabicyclo[3.1.0]hexan-6-yl)carbamate;tert-butyl ((1R,5S,6s)-3-azabicyclo[3.1.0]hexan-6-yl)carbamate;TERT-BUTYL ENDO-3-AZABICYCLO[3.1.0]HEXAN-6-YLCARBAMATE;tert-Butyl(1R,5S,6s)-rel-3-azabicyclo[3.1.0]hexan-6-ylcarbamate;t-Butyl N-[rel-(1R,5S,6S)-3-aZabicyclo[3.1.0]hexan-6-yl]carbamate;tert-Butyl (1R,5S)-3-azabicyclo[3.1.0]hex-6-ylcarbamate, AldrichCPR;(1S,5R,6S)-(3-Aza-bicyclo[3.1.0]hex-6-yl)-carbamic acid tert-butyl ester;N-[(1alpha,5alpha)-3-Azabicyclo[3.1.0]hexan-6alpha-yl]carbamic acid tert-butyl ester;tert-Butyl hydrogen 3-azTert-butyl (1R,5S,6r)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate

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

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 110-111°C
• Refractive Index: 1.513
• Boiling Point: 305.331°C at 760 mmHg
• PKA: 12.39±0.20(Predicted)
• Flash Point: 138.46°C
• PSA: 50.36000
• Density: 1.116g/cm³
• LogP: 1.44860
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO: >20mg/mL
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 198.136827821
• Heavy Atom Count: 14
• Complexity: 237

Purity/Quality:

97% ^*data from raw suppliers

N-(1α,5α,6α)-3-Αzabicyclo[3.1.0]hex-6-yl-carbamicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41-43-48/22
• Safety Statements: 22-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1C2C1CNC2
• Isomeric SMILES: CC(C)(C)OC(=O)NC1[C@H]2[C@@H]1CNC2

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

There total 14 articles about tert-butyl (1R,5S,6r)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate 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: 100.0%

(1α,5α,6α)-3-N-benzyl-6-[t-butoxycarbonylamino]-3-aza-bicyclo[3.1.0]hexane (185559-52-8,151860-18-3) → tert-butyl (1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate (134575-17-0)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 48h;

DOI:10.1016/j.bmcl.2007.10.070

Reference yield:

(1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (146726-08-1) → tert-butyl (1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate (134575-17-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 0 ℃; for 5h;

DOI:10.1016/j.bmcl.2004.03.070

Reference yield:

ethyl (1α,5α,6α)-3-benzyl-3-azabicyclo[3.1.0]hexane-2,4-dione-6-carboxylate (134575-06-7,846024-42-8) → tert-butyl (1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate (134575-17-0)

Guidance literature:

Multi-step reaction with 6 steps

1: LiAlH₄ / tetrahydrofuran / 48 h / Heating

2: H₂ / Pd/C / methanol / 23 h / 0 °C

3: aq. K₂CO₃ / dioxane / 15 h / 20 °C

4: CrO₃; aq. H₂SO₄ / acetone / 2 h / 0 - 20 °C

5: NEt₃; (PhO)2P(O)N₃ / 44 h / Heating

6: H₂ / Pd/C / methanol / 5 h / 0 °C

With chromium(VI) oxide; lithium aluminium tetrahydride; sulfuric acid; diphenyl phosphoryl azide; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; acetone; 4: Jones oxidation;

DOI:10.1016/j.bmcl.2004.03.070

upstream raw materials:

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

(1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

(1α,5α,6α)-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane

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

Downstream raw materials:

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

1-(2,4-difluorophenyl)-7-[(1α,5α,6α)-6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

[(1α,5α,6α)-3-(2-fluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester

[(1α,5α,6α)-3-(4-chlorobenzyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester