Isopropanol → N-[(S)-6-(2-Oxoethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

HRID 1913816Notes

Reaction equation

HRID 1913816 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C@@H:9]([NH:14][C:15](=[O:29])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@@H:24]3[CH2:28][CH2:27][CH2:26][O:25]3)=[CH:18][CH:17]=1)[CH2:8][CH2:7]2)[CH:2]=C.CC([OH:33])C.I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O>[O:33]=[CH:2][CH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C@@H:9]([NH:14][C:15](=[O:29])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@@H:24]3[CH2:28][CH2:27][CH2:26][O:25]3)=[CH:18][CH:17]=1)[CH2:8][CH2:7]2

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 23667635Sodium periodateHCID 67544894N-((S)-6-allyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Product 1

HCID 86645828N-[(S)-6-(2-Oxoethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

A mixture of N-((S)-6-allyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (0.50 g), 2-propanol (50 ml) and water (50 ml) was admixed with sodium periodate (0.60 g) and osmium tetroxide (1.3 mg). After stirring vigorously for 14 hours, the reaction mixture was extracted with ethyl acetate. The organic phase was washed with sodium chloride solution, dried over sodium sulfate and concentrated. The product was thus obtained with the molecular weight of 393.49 (C24H27NO4); MS (ESI): 394 (M+H+).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe product was thus obtained with the molecular weight of 393.49 (C24H27NO4)

Sources & evidence

ORD record
ord-36a631f47e1f48f98ef04a5d17adcd52
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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