Phthalimide → HCID 86681476, compound

HRID 339989Notes

Reaction equation

HRID 339989 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](=[O:23])[N:9]([C@@H:11]([CH2:14][C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=3)[CH2:12]O)[CH2:10][C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:43]1(=[O:53])[NH:47][C:46](=[O:48])[C:45]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:44]12.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](=[O:23])[N:9]([C@@H:11]([CH2:14][C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=3)[CH2:12][N:47]3[C:43](=[O:53])[C:44]4[C:45](=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:46]3=[O:48])[CH2:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86681477HCID 86681477, compound

Product 1

HCID 86681476HCID 86681476, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-2-[(1S)-1-(3,5-difluorobenzyl)-2-hydroxyethyl]-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one (0.340 g, 1.00 mmol), triphenylphosphine (0.263 g, 1.00 mmol) and phthalimide (0.148 g, 1.00 mmol) in tetrahydrofuran (10 mL) at 25° C. was added diethyl azodicarboxylate (0.514 mL, 1.30 mmol). The reaction was stirred at room temperature overnight. After concentration, the residue was purified by combi-flash chromatography eluting with EtOAc/hexane (10-60%). The purification gave 0.360 g (76.7% yield) of the desired product as light green solid. LC/MS found: 468.0 (M+1)+.

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by combi-flash chromatography
  3. washeluting with EtOAc/hexane (10-60%)
  4. customThe purification

Sources & evidence

ORD record
ord-479150d8f8cf43509062fa870e36e89d
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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