HCID 57424224, compound → HCID 11248619, compound

HRID 1765746Notes

Reaction equation

HRID 1765746 reaction equation
C([O:8][C:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]([C:21]2[CH:22]=[C:23]3[C:28](=[C:29]([CH2:31][N:32]([CH:36]4[CH2:38][CH2:37]4)[CH:33]([CH3:35])[CH3:34])[CH:30]=2)[O:27][C:26]([CH3:40])([CH3:39])[CH2:25][C:24]3([CH3:42])[CH3:41])=[O:20])=[CH:14][CH:13]=1)=[O:10])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[C:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]([C:21]2[CH:22]=[C:23]3[C:28](=[C:29]([CH2:31][N:32]([CH:36]4[CH2:37][CH2:38]4)[CH:33]([CH3:35])[CH3:34])[CH:30]=2)[O:27][C:26]([CH3:40])([CH3:39])[CH2:25][C:24]3([CH3:42])[CH3:41])=[O:20])=[CH:14][CH:13]=1)([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 57424224HCID 57424224, compound2×

Product 1

HCID 11248619HCID 11248619, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 8-[(cyclopropyl-isopropyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-carboxylic acid 4-benzyloxycarbonylmethyl-phenyl ester (Intermediate 40, 0.093 g–0.17 mmol) in ethyl acetate (3 mL) was treated with a slurry of 10% palladium on carbon (20 mg) in ethyl acetate and the resulting reaction mixture was stirred under an atmosphere of hydrogen at ambient temperature for 2 h. The reaction mixture was filtered over a bed of celite and the filtrate was evaporated to a residue that was purified by flash column chromatography over silica gel to afford the title compound.

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered over a bed of celite
  3. customthe filtrate was evaporated to a residue that
  4. customwas purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-5a8df48278444311bf19f33bd1282385
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

Loading…