Water → 1-Benzyl-4-(3-phenyl-2-fluoropropyl)piperidine

HRID 380530ノート

反応式

HRID 380530 の反応式
C(N(S(F)(F)[F:7])CC)C.[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH:24](O)[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C(Cl)Cl>[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH:24]([F:7])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 183647871-Benzyl-4-(3-phenyl-2-hydroxypropyl)piperidine

生成物 1

HCID 183647121-Benzyl-4-(3-phenyl-2-fluoropropyl)piperidine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 0.27 mL (2.0 mmol) of (Diethylamino)sulfur trifluoride (DAST) in 2 mL of CH2Cl2 was cooled to −78° C. To this was added a solution of 1-benzyl-4-(3-Phenyl-2-hydroxypropyl)piperidine (Example 228, Step 2) in 2 mL of CH2Cl2. The mixture was stirred and warmed to rt. After 20 min, 10 mL of H2O were added and the mixture was extracted with CH2Cl2. The combined organic fractions were washed with sat'd NaHCO3 solution and sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 1:1) to give 1-benzyl-4-(3-phenyl-2-fluoropropyl)piperidine. Removal of the benzyl protecting group was achieved under standard conditions.

後処理

  1. extractionthe mixture was extracted with CH2Cl2
  2. washThe combined organic fractions were washed with sat'd NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 1:1)

出典と根拠

ORDレコード
ord-ad9d0d5f1b884556a9956c9ac161ea94
出典データセット
uspto-grants-2001_10
特許番号
US06303593B1

反応ノート

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