Ethanolamine → HCID 18345885、化合物

HRID 1522847ノート

反応式

HRID 1522847 の反応式
CS(O[CH2:6][C@H:7]([CH3:15])[CH2:8][CH2:9]OS(C)(=O)=O)(=O)=O.[NH2:16][CH2:17][CH2:18][OH:19].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>C(#N)C.O>[CH3:15][C@@H:7]1[CH2:8][CH2:9][N:16]([CH2:17][CH2:18][OH:19])[CH2:6]1

参加物

7

反応物 4

HCID 700EthanolamineHCID 6344DichloromethaneHCID 11430Potassium Carbonate2 回HCID 10858216HCID 10858216、化合物

生成物 1

HCID 18345885HCID 18345885、化合物収率 28.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of (R)-2-methylbutane-1,4-diyl dimethanesulfonate (30 g, 0.115 mol), 2-aminoethanol (7.0 g, 0.115 mol), and K2CO3 (31.7 g, 0.23 mol) in acetonitrile (0.9 L) was refluxed for 20 h. The mixture was cooled to room temperature and concentrated under vacuum to afford a residue (a mixture of oil and solid). DCM (300 mL) and sat'd K2CO3 solution (300 mL) were added and just enough water was added to dissolve all solid. The organic layer was separated, and aqueous phase was further extracted with DCM (2×300 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography [EA/Hex/MeOH/TEA=10:7:2:1] gave (R)-2-(3-methylpyrrolidin-1-yl)ethanol (4.19 g, 28%). 1H NMR (CDCl3): δ 3.61 (t, 2H), 2.84 (dd, 1H), 2.70 (m, 1H), 2.65 (m, 1H), 2.62 (m, 1H), 2.54 (m, 1H), 2.25 (m, 1H), 2.11 (dd, 1H), 2.03 (m, 1H), 1.36 (m, 1H), 1.03 (d, 3H); MS: 130.2 (M+H)+.

後処理

  1. temperaturewas refluxed for 20 h
  2. concentrationconcentrated under vacuum
  3. customto afford a residue (
  4. additiona mixture of oil and solid)
  5. additionwere added
  6. dissolutionto dissolve all solid
  7. customThe organic layer was separated
  8. extractionaqueous phase was further extracted with DCM (2×300 mL)
  9. dry with materialThe combined organic layers were dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customPurification by flash column chromatography [EA/Hex/MeOH/TEA=10:7:2:1]

出典と根拠

ORDレコード
ord-c3d0d1a0fe0e448796d3a73fa85b55e6
出典データセット
uspto-grants-2015_07
特許番号
US09078871B2

反応ノート

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