Hydrochloric Acid → Methyl 3-(2-aminoethyl)-5,6,7,8-tetrahydroindolizine-2-carboxylate hydrochloride

HRID 592564Notes

Reaction equation

HRID 592564 reaction equation
[C:1]([CH2:3][C:4]1[N:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:6][C:5]=1[C:13]([O:15][CH3:16])=[O:14])#[N:2].[H][H].[ClH:19]>[Pt]=O.C(O)C.C(OCC)(=O)C>[ClH:19].[NH2:2][CH2:1][CH2:3][C:4]1[N:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:6][C:5]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 58044124Methyl 3-(cyanomethyl)-5,6,7,8-tetrahydroindolizine-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 67016117Methyl 3-(2-aminoethyl)-5,6,7,8-tetrahydroindolizine-2-carboxylate hydrochloride

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-(Cyanomethyl)-5,6,7,8-tetrahydroindolizine-2-carboxylate 112b was hydrogenated with platinum oxide catalyst under 50 psi of hydrogen in ethanol and ethyl acetate in the presence of hydrogen chloride overnight at room temperature to give 112c (380 mg, 1.74 mmol) which was used directly in the next step.

Sources & evidence

ORD record
ord-9296158299054182b8d65591eb577f6b
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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