Aluminium lithium hydride → HCID 59814826, compound

HRID 2116642Notes

Reaction equation

HRID 2116642 reaction equation
[F:1][C:2]([F:35])([F:34])[C@:3]([C:10]1[S:14][C:13]([S:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)=[CH:21][C:22](=[O:26])[O:23]3)=[CH:18][CH:17]=2)=[N:12][CH:11]=1)([OH:9])[CH2:4][C:5](OC)=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:9][C@@:3]([C:10]1[S:14][C:13]([S:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)=[CH:21][C:22](=[O:26])[O:23]3)=[CH:18][CH:17]=2)=[N:12][CH:11]=1)([C:2]([F:1])([F:35])[F:34])[CH2:4][CH2:5][OH:6]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59814862HCID 59814862, compound

Product 1

HCID 59814826HCID 59814826, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To methyl(3R)-4,4,4-trifluoro-3-(2-{[4-(4-fluorophenyl)-2-oxo-2H-chromen-7-yl]thio}-1,3-thiazol-5-yl)-3-hydroxybutanoate (0.120 g) in THF at −90° C. was added an ethereal solution of LAH 1.0M (0.29 mL) dropwise. After 25 minutes, the solution was quenched with NH4Cl and brought to rt. After extraction with EtOAc, the solution was dried over MgSO4 and the solvent removed under vacuum. This crude mixture was then treated with NaBH4 in methanol at 0° C. for 15 minute. The mixture was quenched with NH4Cl and extracted with EtOAc. After flash chromatography on silica gel (hexane/EtOAc; 55:45) the title compound was isolated. 1H NMR (400 MHz, acetone-d6): δ 7.90 (s, 1H), 7.68 (m, 2H), 7.62 (s, 1H), 7.56 (dd, 1H), 7.47 (dd, 1H), 7.38 (t, 2H), 6.67 (s, 1H), 6.41 (s, 1H), 4.68 (t, 1H), 3.85 (m, 2H), 2.45 (m, 1H), 2.37 (m, 1H).

Workup

  1. customthe solution was quenched with NH4Cl
  2. custombrought to rt
  3. extractionAfter extraction with EtOAc
  4. dry with materialthe solution was dried over MgSO4
  5. customthe solvent removed under vacuum
  6. additionThis crude mixture was then treated with NaBH4 in methanol at 0° C. for 15 minute
  7. customThe mixture was quenched with NH4Cl
  8. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-49eecb938a3c48d6bf00000bd87af432
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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