Sodium Hydroxide → HCID 57910810, compound

HRID 1968661Notes

Reaction equation

HRID 1968661 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:36][N:35]=[C:34]([C:37](OCC)=[O:38])[CH:33]=2)=[CH:28][CH:27]=1)([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:14][N:13]=1)[CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>C1COCC1.C(OCC)C>[CH3:7][C:8]([C:26]1[CH:27]=[CH:28][C:29]([C:32]2[O:36][N:35]=[C:34]([CH2:37][OH:38])[CH:33]=2)=[CH:30][CH:31]=1)([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:14][N:13]=1)[CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57910774HCID 57910774, compound

Product 1

HCID 57910810HCID 57910810, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (7.80 mL of a 1.0 M solution in THF, 7.80 mmol) was added to a stirred solution of 1c (2.46 g, 5.22 mmol) in diethyl ether (10.0 mL) at 0° C. After approximately 10 min, 1N NaOH was added to quench the reaction followed by dilution with EtOAc. The resulting mixture was dried (magnesium sulfate), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-100% EtOAc/hexanes as eluent) to afford the title compound 1d. m/z (ES) 430 (MH)+. 1HNMR (500 MHz, CDCl3): δ 8.61 (d, 1H, J=4.5 Hz), 8.40 (d, 1H, J=2.5 Hz), 7.75 (m, 1H), 7.67 (d, 211, J=8.5 Hz), 7.53 (d, 1H, J=8.0 Hz), 7.47 (d, 2H, J=8.5 Hz), 7.29 (m, 1H), 7.19 (m, 2H), 6.53 (s, 1H), 5.23 (s, 2H), 4.81 (s, 2H), 3.08 (m, 1H), 1.68 (s, 3H), 0.87 (d, 3H, J=6.6 Hz), 0.80 (d, 3H, J=6.9 Hz).

Workup

  1. customto quench the reaction
  2. dry with materialThe resulting mixture was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-100% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-df4f8f1b6c5b4aea89046ced5589852e
Source dataset
uspto-grants-2013_04
Patent number
US08426413B2

Reaction notes

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