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 1644399Notes

Reaction equation

HRID 1644399 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:21]3[CH:22]=[C:23]([C:26]#[N:27])[CH:24]=[CH:25][C:20]=3[O:19][CH2:18][C:17]2=[O:28])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:31].[Na+].C(OC(=O)NC1CCN(CCN2C3C=C(OC)C=CC=3OCC2=O)C(=O)C1)(C)(C)C>O.[Ru](=O)=O.C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]2[C:21]3[CH:22]=[C:23]([C:26]#[N:27])[CH:24]=[CH:25][C:20]=3[O:19][CH2:18][C:17]2=[O:28])[C:12](=[O:31])[CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

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, 0.21 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-efa4f3bcc635432fb13921a15b692758
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

Loading…