Methylparaben → HCID 24902687, compound

HRID 555385Notes

Reaction equation

HRID 555385 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(P(CCCC)CCCC)CCC.[CH3:29][O:30][C:31](=[O:39])[C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:35]2[CH:36]=[CH:37][C:32]([C:31]([O:30][CH3:29])=[O:39])=[CH:33][CH:34]=2)[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 24902687HCID 24902687, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-Boc-4-piperidinemethanol (10 g, 46.45 mmol) in dry THF (500 mL) was added tributyl phosphine (18.77 g, 92.9 mmol) and 4-hydroxy benzoic acid methyl ester (10.6 g, 69.67 mmol). The reaction mixture was cooled to 0° C. and ADDP (23.41 g, 92.9 mmol) was added dropwise from an addition funnel over a period of 1 hr. The reaction was gradually brought to room temperature and stirring continued for 1 hr. The sol-vent was removed under vacuum and EtOAc (50 mL) was added and cooled to 0° C. The solid formed was filtered and the clear filtrate concentrated and purified by column chromatography (ISCO) using a step gradient starting with heptane going to EtOAc 100%. Desired fractions were collected and the solvent evaporated in vacuo affording 5.9 g (36%) of 4-(4-methoxycarbonyl-phenoxymethyl)-piperidine-1-carboxylic acid t-butyl ester as an oil.

Workup

  1. customwas gradually brought to room temperature
  2. customThe sol-vent was removed under vacuum and EtOAc (50 mL)
  3. additionwas added
  4. temperaturecooled to 0° C
  5. customThe solid formed
  6. filtrationwas filtered
  7. concentrationthe clear filtrate concentrated
  8. custompurified by column chromatography (ISCO)
  9. customDesired fractions were collected
  10. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-1456dfe518b8471db8281d142de7dbdc
Source dataset
uspto-grants-2011_11
Patent number
US08053447B2

Reaction notes

Loading…