Water → HCID 58786406, compound

HRID 1376060Notes

Reaction equation

HRID 1376060 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:15](OC)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH:14]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[CH2:15][OH:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58786589HCID 58786589, compound

Product 1

HCID 58786406HCID 58786406, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cooled solution of the product of Step II (9.75 g, 28.7 mmol) in THF (200 mL) under nitrogen, LAH (2.18 g, 57.4 mmol) was added portionwise. Mixture was allowed to react at room temperature for 20 minutes. Reaction was cooled to 0° C., and H2O (1.6 mL) and 2N NaOH (7 mL) were carefully added. The mixture was stirred for 1 h and filtered through a pad of silica gel and Celite. Solvent was removed under reduced pressure to afford the title compound (96%) as a white solid. MS m/z 313.2 (M++1)

Workup

  1. customto react at room temperature for 20 minutes
  2. customReaction
  3. filtrationfiltered through a pad of silica gel and Celite
  4. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c30614c109064fa88094ec08431e3afb
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

Loading…