Phthalimide → HCID 58929738, compound

HRID 2360269Notes

Reaction equation

HRID 2360269 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[F:13][C:14]1([F:22])[CH2:19][C@H:18]2[CH2:20][C@@H:15]1[CH2:16][C@H:17]2O.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:13][C:14]1([F:22])[CH2:19][C@H:18]2[CH2:20][C@@H:15]1[CH2:16][C@@H:17]2[N:27]1[C:23](=[O:33])[C:24]2[C:25](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:26]1=[O:28]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 589297281044942-90-6

Product 1

HCID 58929738HCID 58929738, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (0.56 mL, 3.6 mmol) in anhydrous THF (3.0 mL) was added drop-wise to a mixture of (1R,2R,4R)-5,5-difluorobicyclo[2.2.1]heptan-2-ol (0.44 g, 3.0 mmol), phthalimide (0.50 g, 3.4 mmol), and triphenyl phosphine (0.78 mL, 3.4 mmol) in anhydrous tetrahydrofuran (15.0 mL) at r.t. under nitrogen. After stirring at ambient temperature for 66 h, the solvents were removed in vacuo. The residue was partitioned between ethyl acetate and water, and the organic portion was separated, washed with brine, and conc. in vacuo. Flash column chromatography (0 to 35% of ethyl acetate in hexanes) gave the title compound as an off-white solid.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe organic portion was separated
  4. washwashed with brine

Sources & evidence

ORD record
ord-e97f7c0b8740415b8218350eba4fc8ba
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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