Ammonium formate → HCID 10103419, compound

HRID 2179408Notes

Reaction equation

HRID 2179408 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH:9]1[C:15]([OH:17])=[O:16])C1C=CC=CC=1.[CH:18]([O-])=O.[NH4+]>CO.[Pd]>[OH:14][CH:11]1[CH2:12][CH2:13][NH:8][CH:9]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 53673348HCID 53673348, compound

Product 1

HCID 10103419HCID 10103419, compoundYield 123%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of the product of step B (600 mg, 2.4 mmol) in methanol (15 mL) was added 10% palladium on carbon (60 mg) and ammonium formate (1.26 g, 20.0 mmol). The reaction mixture was heated to reflux for 2 h, cooled to ambient temperature then filtered through Celite. The filtrate was concentrated in vacuo to afford methyl 4-hydroxypiperidine-2-carboxylate (470 mg, 95%) as a colorless oil which was carried forward without purification: 1H NMR (CDCl3, 400 MHz) δ 3.76-3.74 (m, 4H), 3.44-3.41 (m, 1H), 3.26-3.21 (m, 1H), 2.70-2.63 (m, 1H), 2.33-2.28 (m 1H), 1.91-1.90 (m, 1H), 1.50-1.40 (m, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. filtrationthen filtered through Celite
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9ae698b0d2644112ad5a1bca98b262d3
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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