Ammonium formate → HCID 59032971, compound

HRID 1634756Notes

Reaction equation

HRID 1634756 reaction equation
C([O:8][C:9]1[CH:33]=[CH:32][C:12]([O:13][CH2:14][C@@H:15]([OH:31])[CH2:16][NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])[CH2:21][CH2:20]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[OH:31][C@@H:15]([CH2:16][NH:17][CH2:18][CH:19]1[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][C:27]([F:30])([F:28])[F:29])[CH2:23][CH2:24]1)[CH2:14][O:13][C:12]1[CH:32]=[CH:33][C:9]([OH:8])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10115880HCID 10115880, compound

Product 1

HCID 59032971HCID 59032971, compoundYield 24.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2S)-1-(4-Benzyloxy-phenoxy)-3-{[1-(3,3,3-trifluoro-propyl)-piperidin-4-ylmethyl]-amino}-propan-2-ol (0.20 g, 0.43 mmol) and ammonium formate (0.135 g, 2.15 mmol) in 10 mL of methanol over 0.20 g of 10% palladium on carbon was stirred at ambient temperature for 2 hours. The catalyst was filtered (solka floc) and the filtrate concentrated in vacuo. Crystallization of the crude oil form EtOAc-hexane provided 0.040 g of the title compound as a white solid.

Workup

  1. filtrationThe catalyst was filtered (solka floc)
  2. concentrationthe filtrate concentrated in vacuo
  3. customCrystallization of the crude oil form EtOAc-hexane

Sources & evidence

ORD record
ord-5e4c9f262e5f4215a95e13d16569004c
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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