Water → HCID 59441628, compound

HRID 1014394Notes

Reaction equation

HRID 1014394 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH2:6][C@H:5]1[CH3:15])(=[O:3])[CH3:2].[N:16]([O-:18])=[O:17].[Na+].O>C(O)(C(F)(F)F)=O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=2)[CH2:6][C@H:5]1[CH3:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23668193Sodium NitriteHCID 67317722HCID 67317722, compound

Product 1

HCID 59441628HCID 59441628, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (2R)-1-acetyl-2-methyl-5-(methyloxy)-2,3-dihydro-1H-indole (100 mg, 0.487 mmol)—see (Arp, Forrest O.; Fu, Gregory C. Kinetic Resolutions of Indolines by a Nonenzymatic Acylation Catalyst. Journal of the American Chemical Society (2006), 128(44), 14264-14265.)—in TFA (2 mL) at 0° C. was treated with sodium nitrite (33.6 mg, 0.487 mmol). The resulting red solution was stirred at 0° C. for 1 h. H2O (20 mL) was added, the resulting slurry was filtered and the solids were washed with water to afford (2R)-1-acetyl-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole as a yellow solid (85 mg, 70%). 1H NMR (400 MHz, DMSO-d8) δ ppm 1.22 (d, J=6.41 Hz, 3H), 2.22 (s, 3H), 2.76 (d, J=17.21 Hz, 1H), 3.45 (dd, J=17.12, 8.88 Hz, 1H), 3.89 (s, 3H), 4.59-4.74 (m, 1H), 7.35 (s, 1H), 8.40 (s, 1H); ESIMS (M+H)+=251.00.

Workup

  1. filtrationthe resulting slurry was filtered
  2. washthe solids were washed with water

Sources & evidence

ORD record
ord-2daf02d2dd5e404780252c717318d3bf
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…