Phthalimide → HCID 57691474, compound

HRID 1867650Notes

Reaction equation

HRID 1867650 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([CH2:19][CH2:20]O)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][O:10]1.[C:31]1(=[O:41])[NH:35][C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]12.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[F:26][C:25]([F:27])([F:28])[C:23]1[CH:22]=[C:5]([CH:4]=[C:3]([C:2]([F:30])([F:1])[F:29])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([CH2:19][CH2:20][N:35]2[C:31](=[O:41])[C:32]3[C:33](=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:34]2=[O:36])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][O:10]1

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 5462977Diethyl azodicarboxylateHCID 57691440HCID 57691440, compound

Product 1

HCID 57691474HCID 57691474, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(1-((3,5-bis(trifluoromethyl)benzyloxy)methyl)isochroman-1-yl)ethanol (100 mg, 0.230 mmol), phthalimide (50.8 mg, 0.345 mmol), and tetrahydrofuran (2 mL) at 0° C. was added diethylazodicarboxylate (0.055 mL, 0.345 mmol) dropwise. The ice bath was removed and stirring continued for 1 h. The reaction was quenched by addition of saturated ammonium chloride and extracted with ethyl acetate (2×) which was washed with brine, dried over magnesium sulfate, and concentrated. Column chromatography (8%-->12% EtOAc/Hex) gave 105 mg (81%) as a colorless oil. 1H-NMR (CDCl3, 300 MHz) δ 7.55-7.80 (m, 7H), 7.12 (d, J=7.6 Hz, 1H), 7.01 (m, 3H), 4.66 (qAB, JAB=13.1 Hz, 2H), 4.03 (m, 2H), 3.74 (m, 2H), 3.72 (qAB, JAB=10.4 Hz, 2H), 3.02 (m, 1H), 2.66 (m, 1H), 2.30-2.50 (m, 2H); 13C-NMR (CDCl3, 126 MHz) δ 168.2, 141.2, 136.6, 134.9, 133.7, 132.2, 131.7 (q, J=33.6 Hz), 129.2, 127.4, 126.8, 126.3, 125.5, 123.4 (q, J=273 Hz), 123.0, 121.5, 77.4, 76.1, 72.2, 60.4, 35.5, 33.5, 29.2.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was quenched by addition of saturated ammonium chloride
  3. extractionextracted with ethyl acetate (2×) which
  4. washwas washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customColumn chromatography (8%-->12% EtOAc/Hex) gave 105 mg (81%) as a colorless oil

Sources & evidence

ORD record
ord-f7eb302277bc4abfa33bee4947db7a03
Source dataset
uspto-grants-2009_12
Patent number
US07632861B2

Reaction notes

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