HCID 11127054, compound → HCID 15042723, compound

HRID 1948809Notes

Reaction equation

HRID 1948809 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][C@H: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 11127054HCID 11127054, compound

Product 1

HCID 15042723HCID 15042723, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5R)-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 recrystalisation in dichloromethane, diethyl ether and hexane to furnish the title compound as white needles (1.37 g, 80%); m.p. 82.0-83.0° C. (lit. m.p. 81.0-82.0° C.); v(max)(KBr) 3314 (N—H), 2981 (C—H), 1739 (C═O), cm−1, δH (250 MHz, CDCl3) 7.44-7.33 (5H, m, Ph); 4.42-4.23 (3H, m, CHCH2), 3.88 (1H, q, /6.76 Hz, CHCH3), 1.86 (1H, br, NH), 1.50 (3H, d, J 6.16 Hz, CH3); δc (62.5 MHz, CDCl3) 170.7, 138.0, 129.3, 127.5, 127.2, 75.4, 58.2, 55.4, 19.0 m/z (CL, NH3), 191 (M+, 7%), 147 (20%), 131 (65%), 104 (100%), 91 (20%), and 77 (12%); HRMS for C11H13NO2 requires 191.0943 found 191.0940. [α]D20 −92.9 (c 1.02 CHCl3) (lit. for the enantiomer [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 recrystalisation in dichloromethane

Sources & evidence

ORD record
ord-8f3b07e85c5f4d2fa4659830a1616b19
Source dataset
uspto-grants-2013_03
Patent number
US08399612B2

Reaction notes

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