Water → HCID 59895115, compound

HRID 2185474Notes

Reaction equation

HRID 2185474 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][C:18](=O)[NH:17][C@H:16]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].O>O1CCCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][NH:17][C@H:16]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 57274840HCID 57274840, compound

Product 1

HCID 59895115HCID 59895115, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1.04 g) was added to a solution of (3R)-1-benzyl-3-phenethylpiperazine-2,5-dione (B, 1.68 g) in tetrahydrofuran (60 mL) at 0° C. After stirring at room temperature for 18 hr, anhydrous sodium sulfate and then water were added at 0° C. The insoluble materials were removed by filtration. The resulting mixture was concentrated in vacuo and then partitioned between chloroform and saturated sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the titled compound (1.58 g) as an orange oil, which was used in the next reaction without further purification.

Workup

  1. customThe insoluble materials were removed by filtration
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. custompartitioned between chloroform and saturated sodium hydrogen carbonate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f40eb18b48eb4197954e449fb754851c
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…