Benzyl {(S)-2-[6-(4-benzyloxyphenoxy)pyridin-3-yloxy]-1-methylethyl}carbamate → 4-[5((S)-2-Aminopropoxy)pyridin-2-yloxy]phenol

HRID 1260545Notes

Reaction equation

HRID 1260545 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:12]([O:13][C:14]2[N:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]([NH:24]C(=O)OCC3C=CC=CC=3)[CH3:23])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH2:24][C@@H:22]([CH3:23])[CH2:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([O:13][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:36][CH:35]=2)=[N:19][CH:18]=1

Participants

5

Reactant 2

HCID 86761884Benzyl {(S)-2-[6-(4-benzyloxyphenoxy)pyridin-3-yloxy]-1-methylethyl}carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 670718004-[5((S)-2-Aminopropoxy)pyridin-2-yloxy]phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl {(S)-2-[6-(4-benzyloxyphenoxy)pyridin-3-yloxy]-1-methylethyl}carbamate (118 mg, 0.24 mmol) were hydrogenated in ethanol over 5% of palladium on carbon at 5 bar hydrogen pressure. The catalyst was filtered off and the filtrate was concentrated: Yield: 43 mg (68%), M+H+: 261.13.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5b1d832e9f1942d68545aa0e7bdcfe6b
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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