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

HRID 406619ノート

反応式

HRID 406619 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).

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-6104d52079a84d6ba003c161e2ea972c
出典データセット
uspto-grants-2014_06
特許番号
US08754076B2

反応ノート

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