HCID 12373808, compound → HCID 12413876, compound

HRID 1948815Notes

Reaction equation

HRID 1948815 reaction equation
[CH2:1]([C@@H:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][O:10][C:9]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([C@@H:8]1[NH:13][C@H:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:11][O:10][C:9]1=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 12373808HCID 12373808, compound

Product 1

HCID 12413876HCID 12413876, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3S)-3-Benzyl-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one (1.56 g, 5.88 mmol, 1.0 equiv.) in anhydrous methanol (40 mL) under an atmosphere of nitrogen was added palladium on activated carbon (156 mg, 0.1 equiv. by mass). The mixture was consecutively degassed and purged three times with hydrogen and then stirred for 5 hours under an atmosphere of hydrogen. Filtration through a short pad of CELITE® diatomaceous earth and removal of solvent from the filtrate in vacuo yielded the crude product which was purified by flash column chromatography on silica eluting with petrol and diethyl ether (4:1) to furnish the title product as a white solid (514 mg, 33%); m.p. 75.0-76.0° C. (lit. 76.0-78.0° C.); v(max)(KBr) 3321 (N—H), 2949 (C—H), 1731 (C═O), cm−1; δH (250 MHz, CDCl3) 7.36-7.21 (10H, m, Ph), 4.34-4.15 (3H, m, PhCHCH2), 3.97 (1H, dd, J 3.2, T 10.0 Hz, NHCH), 3.56, (1H, dd, J 3.2, J 13.6 Hz, CHPh×1), 3.00, (1H, dd, /10.0, T 13.6 Hz, CH2Ph×1), 1.84 (1H, br, NH); δH, (62.5 MHz, CDCl3) 169.6, 138.0, 137.8, 129.8, 129.3, 129.2, 129.1, 127.5, 127.4, 75.3, 60.6, 57.9, 39.4; m/z (CL, NH3), 268 (MH+, 40%), 267 (80%, M+), 223 (100%), and 209 (57%); HRMS for C17H17NO2 requires 267.1259 found 267.1263. [α]D20 −156.4 (c 1.02 CHCl3) (lit. [α]D20-157.9 (c 2.00 CHCl3)).

Workup

  1. customThe mixture was consecutively degassed
  2. custompurged three times with hydrogen
  3. filtrationFiltration
  4. customthrough a short pad of CELITE® diatomaceous earth and removal of solvent from the filtrate in vacuo
  5. customyielded the crude product which
  6. customwas purified by flash column chromatography on silica eluting with petrol and diethyl ether (4:1)

Sources & evidence

ORD record
ord-f5e322d1785a478ca3fa5d7ddc665853
Source dataset
uspto-grants-2013_03
Patent number
US08399612B2

Reaction notes

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