Triethylamine → HCID 2057054、化合物

HRID 1888452ノート

反応式

HRID 1888452 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C(N(CC)CC)C.C[C@:18]1([OH:24])[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:20]2[CH2:21][CH2:22][CH2:23][C@H:18]([OH:24])[CH2:19]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 685274-Bromobenzyl bromideHCID 28064083(3S)-3-Methylpiperidin-3-ol

生成物 1

HCID 2057054HCID 2057054、化合物収率 74%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 4-bromobenzyl bromide (1.0 g, 4.0 mmol), triethylamine (0.84 mL, 6.0 mmol) and (S)-3-methyl-piperidin-3-ol (1.11 g, 8.0 mmol) in THF (20 mL) was stirred at ambient temperature for 16 h. The solvent was evaporated and the resultant residue diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over sodium sulfate, filtered and evaporated. The resultant residue was purified by flash chromatography (silica, Biotage 50 g column, 50-100% ethyl acetate in cyclohexane) to afford the title compound (0.8 g, 74%). 1H NMR (CDCl3, 300 MHz): 7.46-7.40 (m, 2H), 7.21-7.14 (m, 2H), 3.85-3.76 (m, 1H), 3.45 (s, 2H), 2.45 (s, 3H), 2.29-2.16 (m, 1H), 1.86-1.70 (m, 1H), 1.67-1.45 (m, 3H) plus 1 exchangeable not observed. LCMS (Method G): RT=1.42 min, M+H+=270.

後処理

  1. customThe solvent was evaporated
  2. additionthe resultant residue diluted with saturated aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resultant residue was purified by flash chromatography (silica, Biotage 50 g column, 50-100% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-8919ea101d334ec09f7ac448d0698f07
出典データセット
uspto-grants-2013_08
特許番号
US08501765B2

反応ノート

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