Phthalimide → HCID 18972484, compound

HRID 2395170Notes

Reaction equation

HRID 2395170 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:31][O:32][C:33]1[CH:34]=[CH:35][C:36]2[N:41]([CH3:42])[C:40]3[CH:43]=[CH:44][C:45]([O:55][CH3:56])=[C:46]([CH2:47][O:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH3:54])[C:39]=3[O:38][C:37]=2[C:57]=1CO.[N+](C(OCC)=O)(C(OCC)=O)=[N-]>O1CCCC1.C(OCC)(=O)C.CO.CCCCCC.O>[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH2:12][N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[C:36]2[N:41]([CH3:42])[C:40]3[CH:43]=[CH:44][C:45]([O:55][CH3:56])=[C:46]([CH2:47][O:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH3:54])[C:39]=3[O:38][C:37]=2[CH:57]=1

Participants

10

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 14357405DiethyldiazodicarboxylateHCID 18972482HCID 18972482, compound

Product 1

HCID 18972484HCID 18972484, compoundYield 93.7%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.63 g (1.5 eq.) of phthalimide and 2.91 g (1.5 eq.) of triphenylphosphine were added portionwise while cooling with ice to a solution of 3.0 g (7.40 mmol) of 3,7-dimethoxy-6-[[(2-methoxyethoxy)methoxy]methyl]-10-methyl-10H-dibenzo[b,e][1,4]oxazine-4-methanol in 40 ml of tetrahydrofuran. Then, a solution of 2.06 g (1.6 eq.) of diethyl diazodicarboxylate in 10 ml of tetrahydrofuran was slowly added dropwise at 0° during 2 hours. The reaction mixture was stirred at 0° for 10 hours and then poured into 50 ml of water, 100 ml of hexane, 50 ml of methanol and 50 ml of ethyl acetate. The organic phase was separated, washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. The residue was chromatographed on 200 g of silica gel with ethyl acetate/hexane (1:1), whereupon 3.61 g (93.7%) of N-[[3,7-dimethoxy-6-[[(2-methoxyethoxy)methoxy]methyl]-10-methyl-10H-dibenzo[b,e][1,4]oxazin-1-yl]methyl]-2,3-dihydro-1H-isoindole-1,3-dione were obtained as an amorphous foam. MS: 534 (M+, 100), 160(8).

Workup

  1. customThe organic phase was separated
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on 200 g of silica gel with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-3a7aa943123e49e699697bea55f0bacd
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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