Cyclohexane → HCID 86730041、化合物

HRID 2199473

反応式

HRID 2199473 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 86730041HCID 86730041、化合物収率 98.7%

試薬・触媒・溶媒 3

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1445f10207fe4433a9bd0f756acc0296
出典データセット
uspto-grants-2016_06
特許番号
US09359286B2

関連ノート

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