Acetic Acid → 4-[(S)-1-(4-Bromo-phenyl)-ethylamino]-1-methoxy-2-phenyl-butan-2-ol

HRID 1046055ノート

反応式

HRID 1046055 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.C(O)(=O)C.[OH:15][C:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH2:20][O:21][CH3:22])[CH2:17][CH:18]=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:18][CH2:17][C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([OH:15])[CH2:20][O:21][CH3:22])[CH3:9])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 596356773-Hydroxy-4-methoxy-3-phenyl-butyraldehyde

生成物 1

HCID 596357994-[(S)-1-(4-Bromo-phenyl)-ethylamino]-1-methoxy-2-phenyl-butan-2-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(S)-1-(4-Bromo-phenyl)-ethylamine (0.93 g), NaB(OAc)3 (0.98 g), and acetic acid (0.27 mL) were added in the given order to a solution of 3-hydroxy-4-methoxy-3-phenyl-butyraldehyde (0.90 g) in tetrahydrofuran (20 mL) at ca. 10-15° C. The cooling bath was removed and the mixture was stirred at room temperature for 2 h. Then, water (50 mL) and 1 M aqueous NaOH solution (20 mL) were added and the resulting mixture was stirred for another 30 min. The mixture was extracted with ethyl acetate and the combined extracts were washed with water and brine. After drying (MgSO4), the solvent was removed to give the title compound which was submitted to the subsequent reaction step without further purification. Yield: 1.80 g (quantitative). Mass spectrum (ESI+): m/z=378/380 (Br) [M+H]+

後処理

  1. customThe cooling bath was removed
  2. additionThen, water (50 mL) and 1 M aqueous NaOH solution (20 mL) were added
  3. stirringthe resulting mixture was stirred for another 30 min
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe combined extracts were washed with water and brine
  6. dry with materialAfter drying (MgSO4)
  7. customthe solvent was removed

出典と根拠

ORDレコード
ord-1c209d81b068442eab848c615b4312c5
出典データセット
uspto-grants-2013_10
特許番号
US08569292B2

反応ノート

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