Hydrochloric Acid → 1-((R)-1-amino-ethyl)-cyclopentanecarbonitrile hydrochloride

HRID 246062Notes

Reaction equation

HRID 246062 reaction equation
[C:1]([C:3]1([C@H:8]([NH:10][S@](C(C)(C)C)=O)[CH3:9])[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[ClH:17]>CO>[ClH:17].[NH2:10][C@@H:8]([C:3]1([C:1]#[N:2])[CH2:7][CH2:6][CH2:5][CH2:4]1)[CH3:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71288952(S)-2-methyl-propane-2-sulfinic acid [(R)-1-(1-cyano-cyclopentyl)-ethyl]-amide

Product 1

HCID 866779391-((R)-1-amino-ethyl)-cyclopentanecarbonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-2-Methyl-propane-2-sulfinic acid [(R)-1-(1-cyano-cyclopentyl)-ethyl]-amide (1.96 g, 8.07 mmol) was dissolved in MeOH (16 mL) and HCl (4.0 M in 1,4-dioxane, 4.0 mL, 16.0 mmol) was added. The reaction mixture was stirred at room temperature for 30 min then concentrated to give 1-((R)-1-amino-ethyl)-cyclopentanecarbonitrile hydrochloride as an off-white solid which was used without further purification.

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-3cbf63dcce604c9592cc755ccf4c49a6
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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