Aluminium lithium hydride → (γS)-4-(Methylsulfonyl)-γ-phenylbenzenepropanol

HRID 1593015Notes

Reaction equation

HRID 1593015 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:12][C:13](N2[C@H](C3C=CC=CC=3)[C@H](C)N(C)C2=O)=[O:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:29]1([C@@H:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)[CH2:12][CH2:13][OH:14])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69264112HCID 69264112, compound

Product 1

HCID 69264553(γS)-4-(Methylsulfonyl)-γ-phenylbenzenepropanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4S,5R)-1-[(S)-3-(4-methanesulfonyl-phenyl)-3-phenyl-propionyl]-3,4-dimethyl-5-phenyl-imidazolidin-2-one (846 mg, 1.78 mmol) in THF (20 mL) at 0° C. was added lithium aluminium hydride (3.6 mL, 1M in THF, 3.6 mmol) and the resulting mixture was stirred for 15 min. The reaction was quenched by the addition of 2M aqueous sodium hydroxide. The phases were separated and the organic phase pre-absorbed onto a Bond Elut and eluted with a gradient of isohexane to ethyl acetate giving the sub-titled compound as a white solid (285 mg, 55%); NMR (CDCl3): 1.63 (br s, 1H), 2.33 (m, 2H), 3.00 (s, 3H), 3.59 (t, 2H), 4.28 (t, 1H), 7.23 (m, 5H), 7.43 (d, 2H), 7.82 (d, 2H).

Workup

  1. customThe reaction was quenched by the addition of 2M aqueous sodium hydroxide
  2. customThe phases were separated
  3. customthe organic phase pre-absorbed onto a Bond Elut
  4. washeluted with a gradient of isohexane to ethyl acetate giving the sub-titled compound as a white solid (285 mg, 55%)

Sources & evidence

ORD record
ord-d5db36baf44d4d229ce0efdac31727f6
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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