Hydrochloric Acid → (cis)-3-(4-Methylthiazol-2-yl)cyclopentanamine hydrochloride

HRID 2404394Notes

Reaction equation

HRID 2404394 reaction equation
[C:1]([C@@H:4]1[CH2:8][CH2:7][C@H:6]([NH:9]C(=O)OC(C)(C)C)[CH2:5]1)(=[S:3])[NH2:2].[Cl:17][CH2:18][C:19](=O)[CH3:20].Cl>C(O)C>[ClH:17].[CH3:20][C:19]1[N:2]=[C:1]([C@@H:4]2[CH2:8][CH2:7][C@H:6]([NH2:9])[CH2:5]2)[S:3][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6571ChloroacetoneHCID 131731762Tert-butyl(cis)-3-carbamothioylcyclopentylcarbamate

Product 1

HCID 68313423(cis)-3-(4-Methylthiazol-2-yl)cyclopentanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Example 120B (100 mg, 0.41 mmol) in ethyl alcohol (3 mL) was added chloroacetone (0.036 mL, 0.45 mmol). The reaction mixture was stirred at reflux overnight, then 2 mL of 2N aqueous HCl was and the mixture was stirred at reflux for 4 h. The mixture was concentrated and the residue triturated in diethyl ether to provide the title compound as a 2:1 cis/trans mixture of diastereomers. MS (ESI+) M/Z 145 [M+H]+.

Workup

  1. temperatureat reflux overnight
  2. stirringthe mixture was stirred
  3. temperatureat reflux for 4 h
  4. concentrationThe mixture was concentrated
  5. customthe residue triturated in diethyl ether

Sources & evidence

ORD record
ord-810dc7ec6f974324b91a70a3c852ed08
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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