Pyridine → HCID 87440141, compound

HRID 2089526Notes

Reaction equation

HRID 2089526 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C@@H:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=O)[CH2:12][C:11]2([CH3:22])[CH3:21])[CH:7]=[N:8][CH:9]=1)=[O:4].Cl.[CH3:24][O:25][NH2:26].N1C=CC=CC=1>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([C@@H:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)/[C:13](=[N:26]/[O:25][CH3:24])/[CH2:12][C:11]2([CH3:22])[CH3:21])[CH:7]=[N:8][CH:9]=1)=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 67547031HCID 67547031, compound

Product 1

HCID 87440141HCID 87440141, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (R)- or (S)-3-(2,2-dimethyl-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester (0.091 g, 0.299 mmol), which can be prepared as described in Example 13, and methoxyamine hydrochloride (0.076 g, 0.897 mmol) in methanol (2 mL) is added pyridine (0.24 g, 2.99 mmol) and the mixture is heated to 50° C. After 1.5 hours, the mixture is diluted with ethyl acetate and washed twice with aqueous copper sulfate, twice with 1:9 v/v aqueous ammonium hydroxide-saturated aqueous ammonium chloride, water, and brine. The organic layer is dried over MgSO4, filtered, and concentrated to furnish (R)- or (S)-3-{4-[(E)-methoxyimino]-2,2-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl}-3H-imidazole-4-carboxylic acid methyl ester as a 19:1 ratio of geometric isomer without the need for further purification. 1H NMR (400 MHz, MeOD) δ ppm 0.94 (s, 3 H), 1.10 (s, 3 H), 2.52 (d, J=17.9 Hz, 1 H), 2.99 (d, J=17.9 Hz, 1 H), 4.03 (s, 3 H), 4.06 (s, 3 H), 6.65 (s, 1 H), 7.17-7.26 (m, 1 H), 7.41-7.49 (m, 2 H), 8.18-8.22 (m, 2 H), 8.27 (br. s., 1 H).

Workup

  1. washwashed twice with aqueous copper sulfate, twice with 1:9 v/v aqueous ammonium hydroxide-saturated aqueous ammonium chloride, water, and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0103cdb3d932425985c1c7ac1413f643
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

Loading…