(5S)-3-methyl-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one → HCID 67442474, compound

HRID 1666922Notes

Reaction equation

HRID 1666922 reaction equation
[CH3:1][C:2]1[C:3](=[O:14])[O:4][CH2:5][C@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1>ClCCl.O=[Pt]=O>[CH3:1][C@@H:2]1[NH:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][O:4][C:3]1=[O:14]

Participants

4

Reactant 1

HCID 57467834(5S)-3-methyl-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one

Product 1

HCID 67442474HCID 67442474, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5S)-3-methyl-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one (1.70 g, 9.0 mmol, 1.0 equiv.) in anhydrous dichloromethane (60 mL) under an atmosphere of nitrogen was added PtO2 (170 mg, 0.1 equiv.). 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 recrystallisation in dichloromethane, diethyl ether and hexane to furnish the title compound as white needles (1.26 g, 74%); m.p. 81.0-82.0° C. (lit. m.p. 81.0-82.0° C.); v(max)(KBr) 3314 (N—H), 2981 (C—H), 1736 (C═O), cm−1; δH (250 MHz, CDCl3) 7.43-7.26 (5H, m, Ph); 4.42-4.23 (3H, m, CHCl2), 3.88 (1H, q, /6.76 Hz, CHCH3), 1.80 (1H, br, NH), 1.50 (3H, d, J 6.76 Hz, CH3); δc (62.5 MHz, CDCl3) 170.7, 138.1, 129.3, 129.1, 127.5, 75.4, 58.2, 55.4, 19.0; m/z (CL, NH3), 192 (MH+, 30%), 147 (68%), 132 (64%), 104 (100%), and 91 (10%); HRMS for C11H13NO2 requires 192.1025 found 192.1019. [α]D20 +88.8 (c 0.96 CHCl3) (lit. [α]D20 +92.3 (c 0.84 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 recrystallisation in dichloromethane

Sources & evidence

ORD record
ord-18f0688b444648f3bae40a71d3a09ab3
Source dataset
uspto-grants-2011_10
Patent number
US08044173B2

Reaction notes

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