Acetic Acid → Acetic acid--tert-butyl 4-carbamimidoylpiperidine-1-carboxylate (1/1)

HRID 419707Notes

Reaction equation

HRID 419707 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[NH:17])[NH:15]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([OH:21])(=[O:20])[CH3:19].C(OC(=O)C)(=O)C>[Pd]>[C:18]([OH:21])(=[O:20])[CH3:19].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[NH:15])[NH2:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 178451986HCID 178451986, compound

Product 1

HCID 66650050Acetic acid--tert-butyl 4-carbamimidoylpiperidine-1-carboxylate (1/1)Yield 126.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Add 10% Pd/C (0.079 g; 37.12 μmoles) to 4-(N-Hydroxycarbamimidoyl)-piperidine-1-carboxylic acid tert-butyl ester (805 mg; 1.00 equiv; 3.31 mmoles) in acetic acid (15 mL; 261.77 mmoles) and acetic acid anhydride (0.5 mL; 5.29 mmoles). Hydrogenate at room temperature for 7 hr at 20 PSI. Purge flask with nitrogen to provide 1.2 g of a foam. Triturate with acetonitrile and filter to provide 270 mg (28%) of the product as a white solid.

Workup

  1. customPurge flask with nitrogen

Sources & evidence

ORD record
ord-1b158131581348e781b2317d8767b659
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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