Ethanolamine → (S)-1,4-dibenzyl-2-(2-(3-fluoro-phenyl)-ethyl)-piperazine

HRID 1350365ノート

反応式

HRID 1350365 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[CH:21]=[CH2:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C12BC(CCC1)CCC2.[F:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35](I)[CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+].C(CN)O>O.C(O)(=O)C.CO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[CH2:21][CH2:22][C:35]1[CH:36]=[CH:37][CH:38]=[C:33]([F:32])[CH:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

10

反応物 6

HCID 700EthanolamineHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 707251-Fluoro-3-iodobenzeneHCID 789669-Borabicyclo(3.3.1)nonaneHCID 17759473(S)-1,4-dibenzyl-2-vinylpiperazine

生成物 1

HCID 69486661(S)-1,4-dibenzyl-2-(2-(3-fluoro-phenyl)-ethyl)-piperazine

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 10129899Acetic acid methanol溶媒

反応条件

温度
60 °C

実験手順

Combine (S)-1,4-dibenzyl-2-vinyl-piperazine (2.0 g, 6.84 mmol) and 9-borabicyclo[3.3.1]nonane (82.1 mL, 41.04 mmol, 0.5 M in THF) and stir at ambient temperature. After 24 hours, add 1-fluoro-3-iodo-benzene (2.3 g, 10.26 mmol), triphenylphosphine (287.0 mg, 1.09 mmol), tetrakis(triphenylphosphine) palladium(0)(158.0 mg, 0.14 mmol), and 3N NaOH (5.6 mL) and stir at 60° C. After 22 hours, add ethanolamine (10.0 mL) and dilute the mixture with water. Extract with ethyl acetate and combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using ethyl acetate/hexanes (5:95) to give a yellow oil. Dissolve the yellow oil in acetic acid/methanol (1:9) and apply to an SCX column. Wash the column with methanol followed by 2N ammonia in methanol to give the title compound: mp 69–71° C.; mass spectrum (ion spray): m/z=389.4 (M+1).

後処理

  1. waitAfter 22 hours
  2. extractionExtract with ethyl acetate and combine
  3. washwash (brine)
  4. dry with materialdry (sodium sulfate)
  5. customPurify the residue on silica gel
  6. customto give a yellow oil
  7. washWash the column with methanol

出典と根拠

ORDレコード
ord-b68636ab99cf45c2b821db7940d0ee48
出典データセット
uspto-grants-2007_05
特許番号
US07214673B2

反応ノート

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