Ethanolamine → HCID 18345885, 화합물

HRID 1522847노트

반응식

HRID 1522847 반응식
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

참가 물질

7

반응물 4

HCID 700EthanolamineHCID 6344DichloromethaneHCID 11430Potassium Carbonate2회HCID 10858216HCID 10858216, 화합물

생성물 1

HCID 18345885HCID 18345885, 화합물수율 28.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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)+.

후처리

  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]

출처 및 근거

ORD 기록
ord-c3d0d1a0fe0e448796d3a73fa85b55e6
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09078871B2

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