Cyclohexane → HCID 86730041, 화합물

HRID 516945

반응식

HRID 516945 반응식
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6][CH2:5]2.C1CCCCC1.[CH3:19][O:20][CH2:21][C@@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[NH2:27].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[N:27][N:23]1[CH2:24][CH2:25][CH2:26][C@H:22]1[CH2:21][O:20][CH3:19])[CH2:7][CH2:6][CH2:5]2

참가 물질

8

반응물 4

HCID 8078CyclohexaneHCID 516892Sodium BicarbonateHCID 7156993(S)-(-)-1-Amino-2-(methoxymethyl)pyrrolidineHCID 454898006-iodo-3,4-dihydronaphthalen-1(2H)-one

생성물 1

HCID 86730041HCID 86730041, 화합물수율 98.7%

시약·촉매·용매 3

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred mixture of 6-iodo-3,4-dihydronaphthalen-1(2H)-one (I-8A, 20.90 g, 77 mmol), p-toluenesulfonic acid monohydrate (0.584 g, 3.07 mmol), and cyclohexane (40 mL) was added (S)-2-(methoxymethyl)pyrrolidin-1-amine (10 g, 77 mmol) dropwise at room temperature under nitrogen. The mixture was heated with azeotropic removal of water for 5 h. The reaction mixture was diluted with ethyl acetate (20 mL) and mixed with saturated aqueous sodium bicarbonate solution (15 mL). The aqueous layer was separated and extracted with ethyl acetate (2×30 mL). The combined organic solutions were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Flash chromatography purification (330 g silica gel column, gradient elution from 0% to 20% EtOAc in hexanes) afforded (S)—N-(6-iodo-3,4-dihydronaphthalen-1(2H)-ylidene)-2-(methoxymethyl)pyrrolidin-1-amine (29.1 g, 76 mmol) as a yellow liquid. LC/MS M+1=385.

후처리

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. dry with materialThe combined organic solutions were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customFlash chromatography purification (330 g silica gel column, gradient elution from 0% to 20% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-344c861f45e644cca4ce7fbb77397d1e
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115054B2

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