Sodium periodate → tert-Butyl {1-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-2-oxopiperidin-4-yl}carbamate

HRID 255280

Reaction equation

HRID 255280 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17][CH2:16]3)[C:7]=2[CH:29]=1)#[N:2].I([O-])(=O)(=O)=[O:31].[Na+].COC1C=CC2OCC(=O)N(CCN3CCC(NC(=O)OC(C)(C)C)CC3=O)C=2C=1>O.[Ru](=O)=O.C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][N:15]3[CH2:16][CH2:17][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:19][C:20]3=[O:31])[C:7]=2[CH:29]=1)#[N:2]

Participants

6

Reactant 3

HCID 23667635Sodium periodateHCID 86642633tert-Butyl {1-[2-(6-methoxy-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-2-oxopiperidin-4-yl}carbamateHCID 86664537tert-Butyl {1-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidin-4-yl}carbamate2×

Product 1

HCID 86642634tert-Butyl {1-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-2-oxopiperidin-4-yl}carbamate

Reagents, catalysts & solvents 2

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 6212ChloroformSolvent

Procedure

tert-Butyl {1-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 59, 835 mg, 2.1 mmol) was reacted with sodium periodate (2.8 g, 13.1 mmol) and ruthenium (IV) oxide hydrate (30 mg, 20.1 mmol) as described for Intermediate 115 for 16 hours, except, chloroform was used for aqueous workup. The product was obtained as a colorless solid, 230 mg (27%).

Workup

  1. customThe product was obtained as a colorless solid, 230 mg (27%)

Sources & evidence

ORD record
ord-c1da0a2867c34614ae6b55b865aac30a
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Linked notes

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