Acetaldehyde → HCID 131728453, compound

HRID 1172483Notes

Reaction equation

HRID 1172483 reaction equation
[CH:1](=O)[CH3:2].[CH3:4][O:5][C:6]([C:8]1[CH:9]=[C:10]([CH3:35])[C:11]2[O:17][C:16]3[C:18]([Cl:31])=[CH:19][C:20]([NH:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:21][C:15]=3[CH2:14][S:13](=[O:33])(=[O:32])[C:12]=2[CH:34]=1)=[O:7].FC(F)(F)C(O)=O.C([BH3-])#N.[Na+]>CO>[CH3:4][O:5][C:6]([C:8]1[CH:9]=[C:10]([CH3:35])[C:11]2[O:17][C:16]3[C:18]([Cl:31])=[CH:19][C:20]([N:22]([CH2:1][CH3:2])[CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:21][C:15]=3[CH2:14][S:13](=[O:33])(=[O:32])[C:12]=2[CH:34]=1)=[O:7]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 131728454HCID 131728454, compound

Product 1

HCID 131728453HCID 131728453, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Acetaldehyde (0.21 mL, 3.80 mmole) was added to a solution of Example 66k (0.370 gm, 0.76 mmol) in dry methanol (15 mL) followed by the addition of trifluoro-acetic acid (0.06 mL, 0.76 mmol). The reaction mixture was stirred at 0° C. for 2 h, allowed to come to room temperature, treated with sodium cyanoborohydride (0.119 g, 1.9 mmol), and stirred overnight. It was concentrated, treated with 10% aqueous sodium bicarbonate solution, water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.3 g, (76.72%); 1H NMR (CDCl3): δ 2.15 (t, 3H, CH3), 2.45-2.55 (m, 6H, 3CH2), 2.70 (s, 3H, CH3), 3.40 (q, 2H, CH2), 3.50 (t, 2H, CH2), 3.70-3.80 (m, 4H, CH2), 3.95 (s, 3H, OCH3), 4.70 (s, 2H, CH2), 6.55 (s, 1H, Ar), 6.70 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.45 (s, 1H, Ar); MS: m/e (CI+) 511 (M−CH3).

Workup

  1. customto come to room temperature
  2. stirringstirred overnight
  3. concentrationIt was concentrated
  4. additiontreated with 10% aqueous sodium bicarbonate solution, water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water, brine
  7. customdried
  8. concentrationconcentrated
  9. custompurified

Sources & evidence

ORD record
ord-86bc384735a2480396e45608c98768b0
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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