Water → HCID 21848650, compound

HRID 618820Notes

Reaction equation

HRID 618820 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[N:21]([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:22][CH2:23][CH2:24][C:25](OCC)=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[S:30]([CH3:33])(=[O:31])=[O:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59941028HCID 59941028, compound

Product 1

HCID 21848650HCID 21848650, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.7 g (12 mmol) of ethyl 4-[(6-benzyloxy-2,2-dimethylchroman-4-yl)-methanesulfonylamino]-N-butyrate (Ex. 28f) were treated with 10 ml of 1 M lithium aluminum hydride solution in THF in 100 ml of THF at 0° C. The mixture was treated at RT with a little water, then with 1N hydrochloric acid, and concentrated, and the residue was extracted three times using EA. After drying and concentrating, the product crystallized overnight. 4.9 g were obtained, m.p. 113-115° C. (from PE/DIPE)

Workup

  1. concentrationwith 1N hydrochloric acid, and concentrated
  2. extractionthe residue was extracted three times
  3. customAfter drying
  4. concentrationconcentrating
  5. customthe product crystallized overnight
  6. custom4.9 g were obtained

Sources & evidence

ORD record
ord-ef16fb1c09be4626901d82bbeb1fb7a3
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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