Water → HCID 57916918, compound

HRID 69460Notes

Reaction equation

HRID 69460 reaction equation
[N:1]1([C@@H:6]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH:26]=[CH:25][C:24]5[C:19](=[CH:20][CH:21]=[C:22](/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH3:31])[CH:23]=5)[C:18]4=[O:32])=[CH:13][C:12]=3[F:33])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C[O:37]CC1.C[N+]1([O-])CCOCC1.[OH2:47]>[Os](=O)(=O)(=O)=O>[N:1]1([C@@H:6]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH:26]=[CH:25][C:24]5[C:19](=[CH:20][CH:21]=[C:22]([C@@H:27]([OH:37])[C@@H:28]([OH:47])[CH2:29][CH2:30][CH3:31])[CH:23]=5)[C:18]4=[O:32])=[CH:13][C:12]=3[F:33])[CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 579166722-((R)-4-[1,3']Bipyrrolidinyl-1'-yl-3-fluorophenyl)-6-((Z)-pent-1-enyl)-2H-isoquinolin-1-one

Product 1

HCID 57916918HCID 57916918, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

Firstly, osmium tetroxide (solution in tert.-butanol, 0.1 equiv.) was added to a mixture of 2-((R)-4-[1,3′]bipyrrolidinyl-1′-yl-3-fluorophenyl)-6-((Z)-pent-1-enyl)-2H-isoquinolin-1-one (0.10 g) and THF (10 mL), and then a solution of N-methyl-morpholine-N-oxide (89 mg) in water (1 mL) was added. After 48 hours the reaction mixture was concentrated and the residue was purified by preparative HPLC. In this way the product was obtained with molecular weight 479.60 (C28H34FN3O3); MS (ESI): 480 (M+H+).

Workup

  1. concentrationAfter 48 hours the reaction mixture was concentrated
  2. customthe residue was purified by preparative HPLC
  3. customIn this way the product was obtained with molecular weight 479.60 (C28H34FN3O3)

Sources & evidence

ORD record
ord-4e2cf9021dc14b3da20a534f7695c029
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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