HCID 59200408, compound → HCID 59200344, compound

HRID 1685319Notes

Reaction equation

HRID 1685319 reaction equation
[OH:1][C:2]([C:22]1[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=1)([C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1)[CH2:3][NH:4]C(=O)OCC1C=CC=CC=1>C(O)C.[Pd]>[NH2:4][CH2:3][C:2]([C:22]1[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=1)([C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1)[OH:1]

Participants

4

Reactant 1

HCID 59200408HCID 59200408, compound

Product 1

HCID 59200344HCID 59200344, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 2-hydroxy-2,2-dim-tolylethylcarbamate (0.309 g, 0.823 mmol) was dissolved in ethanol (6 mL) and treated with 5% Pd/C (˜20 mgs). The reaction was stirred overnight under a hydrogen atmosphere (balloon). The reaction was filtered and the residue was purified on Biotage chromatography (10% to 60% methanol/dichloromethane) to give the title material (0.119 g, 60%) as an oil. 1H NMR (400 MHz, DMSO-d6) δ: 2.24 (6H, s), 3.16 (2H, ddd, J=3.16, 1.77 and 1.64 Hz), 4.27 (2H, s), 6.96 (2H, d, J=7.07 Hz), 7.15 (4H, m), 7.23 (2H, br s). LC/MS (M+H)+: 242. HPLC ret. time (Condition B): 1.328 min.

Workup

  1. filtrationThe reaction was filtered
  2. customthe residue was purified on Biotage chromatography (10% to 60% methanol/dichloromethane)

Sources & evidence

ORD record
ord-7e9c6849f4d0470ab1c66e062c04b5d2
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

Loading…