N,N-Dimethylaniline → (+/-)-(1-Aminomethyl-3,3-dimethyl-cyclopentyl)-acetic acid hydrochloride

HRID 1244832Notes

Reaction equation

HRID 1244832 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:11][CH2:10][C:4]2([CH2:8][NH:7][C:6](=[O:9])[CH2:5]2)[CH2:3]1.C1(C)C=CC(S(NN=CC([Cl:27])=O)(=O)=[O:20])=CC=1.CN(C)C1C=CC=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.C1C=CC=CC=1.C(Cl)(Cl)Cl.C(Cl)Cl>[ClH:27].[NH2:7][CH2:8][C:4]1([CH2:5][C:6]([OH:20])=[O:9])[CH2:10][CH2:11][C:2]([CH3:12])([CH3:1])[CH2:3]1

Participants

9

Reactant 4

HCID 949N,N-DimethylanilineHCID 8471TriethylamineHCID 21923172HCID 21923172, compoundHCID 57296158Glyoxylyl Chloride p-toluenesulfonylhydrazone

Product 1

HCID 69533136(+/-)-(1-Aminomethyl-3,3-dimethyl-cyclopentyl)-acetic acid hydrochloride

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

In step four, the alcohol 4 is treated with glyoxylic acid chloride (p-toluenesulfonyl)hydrazone and N,N-dimethylaniline followed by triethylamine in a solvent such as methylene chloride, chloroform, benzene, or toluene to give the diazoacetate 5.

Sources & evidence

ORD record
ord-73cdc15d1da94f7c8c6c8531d5f9e082
Source dataset
uspto-grants-2006_10
Patent number
US07122678B2

Reaction notes

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