Dimethyl Sulfide → HCID 57433111、化合物

HRID 705170

反応式

HRID 705170 の反応式
S(C)C.[CH3:4][Li].[CH2:6]([N:13]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@@H:14]([CH2:17][CH3:18])[CH:15]=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC>[CH2:19]([N:13]([CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C@@H:14]([CH2:17][CH3:18])[C@H:15]([OH:16])[CH3:4])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 1068Dimethyl SulfideHCID 57433110(S)-2-(dibenzylamino)butanalHCID 178418348HCID 178418348、化合物

生成物 1

HCID 57433111HCID 57433111、化合物収率 89.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a stirred suspension of CuBr.SMe2 (1.54 g, 7.5 mmol) in anhydrous ether under an argon atmosphere at −78° C., was added methyllithium (1.6M in ether, 9.4 ml, 15 mmol) dropwise. After the addition was complete, the reaction was allowed to warm to room temperature. The reaction was recooled to −78° C. and a solution of (S)-2-(dibenzylamino)butanal (1 g, 3.75 mmol) in ether (20 ml) was added dropwise. After the addition, continued stirring for 2 h The reaction was then quenched with a saturated aqueous solution of NH4Cl (10 ml). The reaction mixture was extracted with ether (2×30 ml) and the combined organic phase washed with brine (20 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by flash silica gel gradient column chromatography, eluted with hexane:ethyl acetate (100:0→80:20) to afford the product as a light yellow oil (0.95 g, 89%) as the only isomer. δH (250 MHz, CDCl3) 1.05 (3 H, t, J 7.5, CHCH2CH3), 1.25 [3 H, d, J 7.5, CH(CH3)OH], 1.6-1.49 (1 H, m, CHHCH3), 1.88-1.73 (1 H, m, CHHCH3), 2.41 (1 H, s, br, OH), 2.66-2.59 (1 H, m, CHCH2CH3), 3.85-3.65 (4 H, m, 2×CH2Ph), 4.05-3.9 (1 H, m, CHOH), 7.41-7.25 (10 H, m, ArH) δC (250 MHz, CDCl3) 140.05 (2×C), 128.98 (4×CH), 128.37 (4×CH), 127.3 (2×CH), 66.81 (CH), 63.65 (CH), 55.41 (CH2), 20.63 (CH3) 18.44 (CH2), 12.5 (CH3)

後処理

  1. additionAfter the addition
  2. customwas recooled to −78° C.
  3. additionAfter the addition
  4. customwas then quenched with a saturated aqueous solution of NH4Cl (10 ml)
  5. extractionThe reaction mixture was extracted with ether (2×30 ml)
  6. washthe combined organic phase washed with brine (20 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. customThe residue was purified by flash silica gel gradient column chromatography
  10. washeluted with hexane:ethyl acetate (100:0→80:20)

出典と根拠

ORDレコード
ord-9e9e4051bba84ac9b42ef7dc3468cc2f
出典データセット
uspto-grants-2015_11
特許番号
US09173938B2

関連ノート

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