Ammonia methanol → HCID 42610749, compound

HRID 2098515Notes

Reaction equation

HRID 2098515 reaction equation
[OH:1][C:2]([C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)[CH:11]=[CH:12][CH:13]=1)([CH2:4][CH2:5][CH2:6][CH3:7])[CH3:3].N.CO>C(OCC)(=O)C>[NH2:17][CH2:16][CH2:15][CH2:14][C:10]1[CH:9]=[C:8]([C:2]([OH:1])([CH2:4][CH2:5][CH2:6][CH3:7])[CH3:3])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 66743673HCID 66743673, compound

Product 1

HCID 42610749HCID 42610749, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Deprotection of 2-(3-(3-(2-hydroxyhexan-2-yl)phenyl)propyl)isoindoline-1,3-dione followed by flash chromatography (0-10% (7N NH3/MeOH)/ethyl acetate gradient), gave Example 120 a colorless oil. Yield (0.157 g, 90%): 1H NMR (400 MHz, CDCl3) δ 7.20-7.27 (m, 3H), 7.03-7.07 (m, 1H), 2.73 (t, J=7.2 Hz, 2H), 2.66 (t, J=8.0 Hz, 2H), 1.70-1.84 (m, 4H), 1.53 (s, 3H), 1.42 (brs, 3H), 1.18-1.30 (m, 3H), 1.06-1.16 (m, 1H), 0.84 (t, J=7.2 Hz, 3H). ESI MS m/z 236.2 [m+H]+, 218.2 [m+H—H2O].

Workup

  1. customgave Example 120 a colorless oil
  2. customYield (0.157 g, 90%)

Sources & evidence

ORD record
ord-bfd487cd6b7e4b23b4baabd847286717
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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