Water → HCID 18612673, compound

HRID 1264535Notes

Reaction equation

HRID 1264535 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([CH2:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)[C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=1)C.[H-].[Al+3].[H-].[H-].C(OCC)C.O>O1CCCC1>[C:19]1([CH2:18][N:6]([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=2)[CH2:5][CH2:4][OH:3])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl Ether2×HCID 21584524AluminiumhydrideHCID 70025487HCID 70025487, compound

Product 1

HCID 18612673HCID 18612673, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

[Naphthalen-1-ylmethyl-(3-phenyl-isoxazol-5-yl)-amino]-acetic acid ethyl ester (305 mg, 0.789 mmol) was dissolved in tetrahydrofuran (THF, 2 ml) and while stirring under argon, treated with a 1.0M ithium aluminum hydride in di ethyl ether solution (1.58 ml, 1.58 mmol) and stirred at rt for 1.5 hr. The reaction was diluted with THF (2 ml), followed by diethyl ether (10 ml), and water was added slowly dropwise to give a filterable solid. The mixture was filtered through super cel, the filter cake washed well with a THF/diethyl ether (1/4), and the filtrate stripped to dryness in vacuo to give a crude oil (200 mg). Flash chromatography on silica gel (10 to 15% diethyl ether in methylene chloride) gave the product as a white foam (179 mg, 65.9%).

Workup

  1. stirringstirred at rt for 1.5 hr
  2. additionwas added slowly dropwise
  3. customto give a filterable solid
  4. filtrationThe mixture was filtered through super cel
  5. washthe filter cake washed well with a THF/diethyl ether (1/4)
  6. customto give a crude oil (200 mg)

Sources & evidence

ORD record
ord-8d1a27e081204ab8b03531c2a53d37e6
Source dataset
uspto-grants-2003_04
Patent number
US06544982B1

Reaction notes

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