Phthalimide → HCID 69332185, compound

HRID 354420Notes

Reaction equation

HRID 354420 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10](O)[CH2:11][CH2:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:35]1(=[O:45])[NH:39][C:38](=[O:40])[C:37]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:36]12.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[CH2:1]([O:8][CH2:9][C@@H:10]([N:39]1[C:38](=[O:40])[C:37]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:36]2[C:35]1=[O:45])[CH2:11][CH2:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 14752582HCID 14752582, compound

Product 1

HCID 69332185HCID 69332185, compoundYield 83.8%

Procedure

To a stirred solution of 1-benzyloxy-2-(R)-hydroxy-5-hexene (2.18 g, 10.5 mmol), triphenylphosphine (3.32 g, 12.7 mmol) and phthalimide (1.86 g, 12.7 mmol) was added diisopropyl azodicarboxylate (2.62 ml, 12.7 mmol) at rt, and the resulting mixture was stirred for overnight at rt. The mixture was concentrated in vacuo and extracted with EtOAc. The organic layer was washed with water, drying over anhydrous Na2SO4, then concentrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (5:1) as eluent to give 1-benzyloxy-2-(S)-phthalimido-5-hexene (2.95 g, 83%) as a colorless oil: 1H-NMR (CDCl3) δ1.76-1.84 (m, 2 H), 2.06 (dd, J 14.4, 6.8 Hz), 2 H, 2.12-2.22 (m, 1 H), 3.69 (dd, J=10.0, 5.6 Hz, 1 H), 4.00 (t, J=9.6 Hz, 1 H), 4.46 (d, J=12.0 Hz, 1 H), 4.53 (d, J=12.0 Hz, 1 H), 4.51-4.58 (m, 1H), 4.91-4.99 (series of m, 2 H), 5.72-5.79 (m, 1 H)7.21-7.26 (m, 5 H), 7.71-7.83 (series of m, 2 H); MS (ESI) m/z, 336 (M++MH).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialdrying over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel with hexane-EtOAc (5:1) as eluent

Sources & evidence

ORD record
ord-712b4cf8f26a405fa56759ae44f6d76f
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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