HCID 11096167, compound → HCID 11830202, compound

HRID 1637046Notes

Reaction equation

HRID 1637046 reaction equation
C[O:2][C:3](=O)[CH2:4][C@@H:5]([NH:7][C@@H:8]([CH3:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6].C[Mg]Br>C(OCC)C>[CH3:15][C@H:8]([N:7]1[C@@H:5]([CH3:6])[CH2:4][C:3]1=[O:2])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 11096167HCID 11096167, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 11830202HCID 11830202, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution compound (35) from Example 21 (1.00 mmol) in anhydrous diethyl ether (5 ml) at 0° C. was added slowly, dropwise, 3.0 M methylmagnesium bromide (1.10 mmol). The resulting solution was stirred for 10 minutes and the reaction was then quenched by addition of pH7 buffer. Diethyl ether (20 ml) was added, whereafter the solution was washed with water (20 ml) and brine (20 ml), dried (magnesium sulphate) and filtered. The solvent was removed under reduced pressure to afford the title compound (41) as a clear oil which was subjected to flash chromatography on silica gel. [α]D21 -68.9 (c 1.61, CHCl3); νmax (CHCl3)/cm-1 1742 s (C=O), δH (300 MHz; CDCl3) 7.34-7.23(5H, m, Ph), 4.92 (1H, q, J=7.2, PhCHCH3), 3.51 (1H, m, CH3CHCH2); 2.97, 2.46 (2H, ABX system, JAB =14.4, JAX =5.1, JBX =2.4, CH2CO), 1.63 (3H, d, J=7.2, PhCHCH3), 1.25 (3H, d, J=6.1, CH3CHCH2); δC (50 MHz; CDCl3) 166.90 (C=O), 140.67 (Ph:Cipso), 128.85, 127,18 (Ph:Cortho,Cmeta), 127.77 (Ph: Cpara), 51.78, 47.18 (CHN), 43.45(CH2CO), 20.65, 19.25 (NCHCH3); m/z (CI) 190 (MH+, 100%), 174(5), 132 (10), 105 (8); (Found: C, 76.02; H, 7.98; 7.07. C12H15NO requires C, 76.16; H, 7.99; N, 7.40%).

Workup

  1. customthe reaction was then quenched by addition of pH7 buffer
  2. additionDiethyl ether (20 ml) was added, whereafter the solution
  3. washwas washed with water (20 ml) and brine (20 ml)
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dbc7dc97ba914fc794e8005c19f34ca0
Source dataset
uspto-grants-2000_03
Patent number
US06037498

Reaction notes

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