Tert-butyl 4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylate → tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

HRID 1063378Notes

Reaction equation

HRID 1063378 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[C:15][CH2:16][OH:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.O=[Pt]=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 69786345Tert-butyl 4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylate

Product 1

HCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylateYield 99.3%

Reagents, catalysts & solvents 2

HCID 11139377Platinum dioxide monohydrateCatalystHCID 702EthanolSolvent

Procedure

1.63 g (6.83 mmol) of 4-(3-Hydroxy-prop-1-ynyl)-piperidine-1-carboxylic acid tert-butyl ester was dissolved in 50 ml of ethanol, treated with 350 mg of PtO2.H2O and hydrogenated (1 atm) for 7 h. The reaction was filtered and evaporated to give 1.65 g (99%) of 4-(3-Hydroxy-propyl)-piperidine-1-carboxylic acid tert-butyl ester, MS: 244 (MH1, 1Cl).

Workup

  1. filtrationThe reaction was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-f5ebf4c08e2443828d823c135a3afc54
Source dataset
uspto-grants-2005_11
Patent number
US06964974B2

Reaction notes

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