(1R,2S)-2-[[(3S)-3-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]cyclohexan-1-amine

Base Information

• Chemical Name: (1R,2S)-2-[[(3S)-3-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]cyclohexan-1-amine
• CAS No.: 275815-63-9
• Molecular Formula: C₁₉H₂₉FN₂
• Molecular Weight: 304.451
• DSSTox Substance ID: DTXSID20457390
• Mol file: 275815-63-9.mol

Synonyms:275815-63-9;CTK4F9921;DTXSID20457390;AKOS015963758;(1R,2S)-2-[[(3S)-3-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]cyclohexan-1-amine

Chemical Property of (1R,2S)-2-[[(3S)-3-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]cyclohexan-1-amine

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 304.23147710
• Heavy Atom Count: 22
• Complexity: 327

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)CN2CCCC(C2)CC3=CC=C(C=C3)F)N
• Isomeric SMILES: C1CC[C@H]([C@@H](C1)CN2CCC[C@H](C2)CC3=CC=C(C=C3)F)N

Technology Process of (1R,2S)-2-[[(3S)-3-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]cyclohexan-1-amine

There total 10 articles about (1R,2S)-2-[[(3S)-3-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]cyclohexan-1-amine 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:

{(1R,2S)-2-[(S)-3-(4-Fluoro-benzyl)-piperidin-1-ylmethyl]-cyclohexyl}-carbamic acid benzyl ester (383430-26-0) → (1R,2S)-2-(((S)-3-(4-fluorobenzyl)piperidin-1-yl)methyl)cyclohexylamine (275815-63-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 2585.74 Torr;

DOI:10.1021/jm049530m

Reference yield:

(1R,2R)-2-(benzyloxycarbonylamino)cyclohexanecarboxaldehyde (275815-60-6) → (1R,2S)-2-(((S)-3-(4-fluorobenzyl)piperidin-1-yl)methyl)cyclohexylamine (275815-63-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 32.1 g / NaBH(OAc)3 / CH₂Cl₂ / 20 °C

2: H₂ / Pd/C / methanol / 2585.74 Torr

With hydrogen; sodium tris(acetoxy)borohydride; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jm049530m

Reference yield:

trans-(1R,2R)-1-amino-2-hydroxymethyl-cyclohexane (178737-10-5) → (1R,2S)-2-(((S)-3-(4-fluorobenzyl)piperidin-1-yl)methyl)cyclohexylamine (275815-63-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 16.3 g / aq. Na₂CO₃ / CH₂Cl₂ / 1 h / 20 °C

2: 30.7 g / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂

3: 32.1 g / NaBH(OAc)3 / CH₂Cl₂ / 20 °C

4: H₂ / Pd/C / methanol / 2585.74 Torr

With oxalyl dichloride; hydrogen; sodium tris(acetoxy)borohydride; sodium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; 2: Swern oxidation;

DOI:10.1021/jm049530m

upstream raw materials:

{(1R,2S)-2-[(S)-3-(4-Fluoro-benzyl)-piperidin-1-ylmethyl]-cyclohexyl}-carbamic acid benzyl ester

(1R,2R)-2-(benzyloxycarbonylamino)cyclohexanecarboxaldehyde

trans-(1R,2R)-1-amino-2-hydroxymethyl-cyclohexane

N-benzyl-3-piperidinone hydrochloride