Sodium Hydroxide → HCID 45139977, compound

HRID 574299Notes

Reaction equation

HRID 574299 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([N:19]([CH2:29][CH2:30][CH3:31])[C:20](=O)[CH2:21][N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH2:16]2)=[CH:11][CH:10]=1.[OH-].[Na+]>C1COCC1>[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([N:19]([CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]3)[CH2:29][CH2:30][CH3:31])[CH2:16]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 45139976HCID 45139976, compound

Product 1

HCID 45139977HCID 45139977, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of LiAlH4 (1.6 g, 40.5 mmol) in THF (100 ml) in an ice bath was added 37a (3.8 g, 11.0 mmol) dissolved in a solution of THF (25 ml). After addition, the mixture was refluxed for 3 hrs and cooled to 0° C. 10% NaOH was added dropwise, and the mixture stirred for 20 min, and filtered. The solution was dried (Na2SO4), filtered, and concentrated to give 38a (3.21 g, 97%), which was used without further purification. 1H NMR (400 MHz, CDCl3) 0.91-0.96 (t, 3H, J=7.6 Hz), 1.40-1.59 (m, 3H), 1.97-2.22 (m, 1H), 2.41-3.11 (m, 19H), 3.82 (s, 3H), 5.2 (bs, 1H), 6.61-6.62 (dd, 1H, J=1.6 Hz), 6.66-6.79 (m, 1H), 6.96-6.99 (d, 1H, J=8.8 Hz).

Workup

  1. additionAfter addition
  2. temperaturethe mixture was refluxed for 3 hrs
  3. filtrationfiltered
  4. dry with materialThe solution was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d73909fabb264db1bec4beaebcc9d1b8
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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