Isopropanol → N-((R)-5-Formylindan-2-yl)-5-[(S)-1-(tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxamide

HRID 1039638Notes

Reaction equation

HRID 1039638 reaction equation
C([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]3[CH2:27][CH2:26][CH2:25][O:24]3)=[CH:17][N:16]=1)=[O:14])[CH2:6]2)=C.C[CH:29]([OH:31])C.I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O>[CH:29]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]3[CH2:27][CH2:26][CH2:25][O:24]3)=[CH:17][N:16]=1)=[O:14])[CH2:6]2)=[O:31]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 23667635Sodium periodateHCID 66679809N-((R)-5-vinylindan-2-yl)-5-[(S)-1-(tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxamide

Product 1

HCID 86762098N-((R)-5-Formylindan-2-yl)-5-[(S)-1-(tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

A mixture of N-((R)-5-vinylindan-2-yl)-5-[(S)-1-(tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxamide (0.60 g) and 2-propanol (5 ml) was admixed with a mixture of sodium periodate (0.775 g) and water (3 ml). Osmium(VIII) oxide (solution in tert-butanol; 16.7 mg) was added and the mixture was stirred vigorously for 3 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. This afforded the product with the molecular weight of 366.42 (C21H22N2O4); MS (ESI): 367 (M+H+).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThis afforded the product with the molecular weight of 366.42 (C21H22N2O4)

Sources & evidence

ORD record
ord-03dc910102a640789dc4d505790247a1
Source dataset
uspto-grants-2013_10
Patent number
US08552199B2

Reaction notes

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