Water → HCID 59701420, compound

HRID 902657Notes

Reaction equation

HRID 902657 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C@H:12]([CH3:37])[CH2:13][CH2:14][N:15]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[C:27]=2[Cl:36])[CH2:16][C@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C.O>C1COCC1>[Cl:36][C:27]1[C:28]([C:32]([F:33])([F:34])[F:35])=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][N:15]([CH2:16][C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18])[CH2:14][CH2:13][C@@H:12]([CH3:37])[O:11][C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][OH:2])[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 69251136HCID 69251136, compound

Product 1

HCID 59701420HCID 59701420, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl]((S)-2-phenyl-propyl)amino]-(R)-1-methyl-propoxy}phenyl)acetic acid methyl ester (20 mg, 0.036 mmol) in THF (1 ml) at 0° C., was treated with LiAlH4 (100 uL of a 1N solution in THF), and the reaction was stirred at 0° for 45 minutes. Ethyl acetate (1 ml) was added, the reaction warmed to RT, and water (2 ml) was added. The mixture was extracted with ethyl acetate. The organic extracts were dried and the solvent removed. The residue was chromatographed over silica gel (hexane/Ethyl acetate:3/7) to give the title compound as a pure oil (15 mg, 91%). MS (ESI) 520.0 (M+H)+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customThe organic extracts were dried
  3. customthe solvent removed
  4. customThe residue was chromatographed over silica gel (hexane/Ethyl acetate:3/7)

Sources & evidence

ORD record
ord-bbf25b8b72a047ad898d0bb8fca6e434
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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