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Water → N-((S)-6-Formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methyl-5-cyclopropylmethoxypyridine-2-carboxamide

HRID 77425
Notes
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Reaction equation

HRID 77425 reaction equation
[CH3:1][N:2]([C@H:16]1[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH:26]=C)[CH:22]=2)[CH2:17]1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH:13]2[CH2:15][CH2:14]2)=[CH:7][N:6]=1)=[O:4].CC([OH:31])C.O.I([O-])(=O)(=O)=O.[Na+]>C(=O)([O-])[O-].[Na+].[Na+].[Os](=O)(=O)(=O)=O>[CH:26]([C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[CH2:17][C@@H:16]([N:2]([CH3:1])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH:13]3[CH2:15][CH2:14]3)=[CH:7][N:6]=1)=[O:4])[CH2:25][CH2:24]2)=[O:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 23667635Sodium periodateHCID 66663592N-methyl-N-((S)-6-vinyl-1,2,3,4-tetrahydronaphthalen-2-yl)-5-cyclopropylmethoxypyridine-2-carboxamide

Product 1

HCID 86661275N-((S)-6-Formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methyl-5-cyclopropylmethoxypyridine-2-carboxamide

Reagents, catalysts & solvents

2
HCID 30318Osmium TetroxideCatalystHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of N-methyl-N—((S)-6-vinyl-1,2,3,4-tetrahydronaphthalen-2-yl)-5-cyclopropylmethoxypyridine-2-carboxamide (1.40 g), 2-propanol (4 ml) and water (2 ml) was admixed with osmium(VIII) oxide (49 mg) and sodium metaperiodate (1.82 g), and the mixture was stirred for 12 hours. The reaction mixture was diluted with saturated sodium carbonate solution and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated. The product was thus obtained with the molecular weight of 364.45 (C22H24N2O3); MS (ESI): 365 (M+H+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was thus obtained with the molecular weight of 364.45 (C22H24N2O3)

Sources & evidence

ORD record
ord-d405832cc9a34d8991d0b70915cde459
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841290B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes