Aluminium lithium hydride → HCID 86603188, compound

HRID 1818962Notes

Reaction equation

HRID 1818962 reaction equation
C[O:2][C:3](=O)[CH:4]([C:17]1[S:21][C:20]([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)=[O:24])=[N:19][CH:18]=1)[CH2:5][O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:2][CH2:3][CH:4]([C:17]1[S:21][C:20]([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=2)=[O:24])=[N:19][CH:18]=1)[CH2:5][O:6][Si:7]([CH:14]([CH3:15])[CH3:16])([CH:11]([CH3:12])[CH3:13])[CH:8]([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86603187HCID 86603187, compound

Product 1

HCID 86603188HCID 86603188, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of compound 73.2 (0.275 mmol) in THF (2.5 mL) was added LAH (0.275 mL of a 1.0 M solution in THF) dropwise at 0° C. The reaction is allowed to warmed to room temperature and stirred until the starting material was consumed. The reaction is quenched by the dropwise addition of water and the reaction mixture was extracted with EtOAc. The combined organic layers were combined, dried and concentrated to give a residue that was purified by flash column chromatography (20 to 100% EtOAc in hexanes) to provide 1-[5-(2-hydroxy-1-triisopropylsilanyloxymethyl-ethyl)-thiazol-2-yl]-3-(3-trifluoromethyl-phenyl)-urea (compound 73.3).

Workup

  1. customwas consumed
  2. customThe reaction is quenched by the dropwise addition of water
  3. extractionthe reaction mixture was extracted with EtOAc
  4. customdried
  5. concentrationconcentrated
  6. customto give a residue that
  7. customwas purified by flash column chromatography (20 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8f20bdaa6f9c4cbc8daa95c29f58a5fa
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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