Ammonium formate → HCID 57989160, compound

HRID 1689522Notes

Reaction equation

HRID 1689522 reaction equation
Cl.C1([C@H]([NH:10][C@H:11]([CH3:21])[CH2:12][C:13]2[CH:14]=[C:15]([CH2:19][OH:20])[CH:16]=[CH:17][CH:18]=2)C)C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:10][C@H:11]([CH3:21])[CH2:12][C:13]1[CH:14]=[C:15]([CH2:19][OH:20])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67291735HCID 67291735, compound

Product 1

HCID 57989160HCID 57989160, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of (3-((R)-2-((R)-1-phenylethylamino)propyl)phenyl)methanol hydrochloride (Example 276, step b) (1.92 g), 20% palladium hydroxide on carbon (0.757 g) and ammonium formate (2.28 g) in ethanol (30 mL) was stirred at 75° C. for 1.5 hours, then allowed to cool. The suspension was filtered through diatomaceous earth, washing the residue well with ethanol. The combined filtrate and washings were concentrated in vacuo to afford a pale yellow gum as a mixture of desired product and des-hydroxy analogue. Yield 1.54 g. Used directly

Workup

  1. temperatureto cool
  2. filtrationThe suspension was filtered through diatomaceous earth
  3. washwashing the residue well with ethanol
  4. concentrationThe combined filtrate and washings were concentrated in vacuo
  5. customto afford a pale yellow gum

Sources & evidence

ORD record
ord-a51d604f60c549b293d91583c3ca9efc
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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