Sodium Hydroxide → 7a-ethynylhexahydro-1H-pyrrolizine

HRID 3300

반응식

HRID 3300 반응식
Cl([O-])(=O)(=O)=O.[CH+:6]1[CH:13]2[N:9]([CH2:10][CH2:11][CH2:12]2)[CH2:8][CH2:7]1.[C:14]([Mg]Br)#[CH:15].[OH-].[Na+]>C1COCC1.[Cl-].[Na+].O.O>[C:14]([C:13]12[CH2:12][CH2:11][CH2:10][N:9]1[CH2:8][CH2:7][CH2:6]2)#[CH:15]

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 867523401,2,3,5,6,7-Hexahydropyrrolizinylium perchlorateHCID 178418486HCID 178418486, 화합물

생성물 1

HCID 195976957a-ethynylhexahydro-1H-pyrrolizine수율 71.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 23713072Sodium chloride dihydrate용매

실험 절차

1,2,3,5,6,7-Hexahydropyrrolizinylium perchlorate (1.0 g, 4.8 mmol) was added to a solution of 0.5M ethynylmagnesium bromide (29 mL, 14.3 mmol) in THF at room temperature. The reaction mixture was allowed to stir for 45 minutes, and 15% NaOH solution was added. The slurry was diluted with brine:water (1:1) and extracted with CH2Cl2 (3×). The organic phases were combined, dried (MgSO4), concentrated and chromatographed (silica gel; CHCl3 /MeOH, 90:10) to afford an amber oil (463 mg, 71%): 1H NMR (CDCl3, 300 MHz) δ1.75-2.06 (m, 6H), 2.14-2.23 (m, 2H), 2.33 (s, 1H), 2.53-2.62 (m, 2H), 3.22-3.28 (m, 2H); MS (Cl/NH3) m/z: 136 (M+H)+.

후처리

  1. extractionextracted with CH2Cl2 (3×)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customchromatographed (silica gel; CHCl3 /MeOH, 90:10)

출처 및 근거

ORD 기록
ord-eafa3d7b107148f580724adaf23e414c
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733912

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