Ammonia methanol → HCID 42610750, compound

HRID 2098516Notes

Reaction equation

HRID 2098516 reaction equation
[OH:1][C:2]([CH3:28])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][CH2:12][N:13]2C(=O)C3C(=CC=CC=3)C2=O)[CH:7]=[CH:8][CH:9]=1.N.CO>C(OCC)(=O)C>[NH2:13][CH2:12][CH2:11][CH2:10][C:6]1[CH:5]=[C:4]([CH2:3][C:2]([CH3:28])([OH:1])[CH2:24][CH2:25][CH2:26][CH3:27])[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 66743998HCID 66743998, compound

Product 1

HCID 42610750HCID 42610750, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Deprotection of 2-(3-(3-(2-hydroxy-2-methylhexyl)phenyl)propyl)isoindoline-1,3-dione followed by flash chromatography (0-10% (7N NH3/MeOH)/ethyl acetate) gradient gave Example 121 a colorless oil. Yield (0.144 g, 85%): 1H NMR (400 MHz, CDCl3) δ 7.18-7.24 (m, 1H), 7.00-7.08 (m, 3H), 2.68-2.78 (m, 4H), 2.60-2.68 (m, 2H), 1.71-1.80 (m, 2H), 1.24-1.50 (m, 9H), 1.12 (s, 3H), 0.91 (t, J=7.2 Hz, 3H). ESI MS m/z 250.3 [m+H]+, 232.3 [m+H—H2O]

Workup

  1. customgave Example 121 a colorless oil
  2. customYield (0.144 g, 85%)

Sources & evidence

ORD record
ord-9d048ba9533242649db4265f5b7fab51
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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