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

HRID 1593015노트

반응식

HRID 1593015 반응식
[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

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 69264112HCID 69264112, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-d5db36baf44d4d229ce0efdac31727f6
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07294636B2

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