Tributylphosphine → 6-(3-Piperidin-1-yl-propoxy)-naphthalene-2-carboxylic acid methyl ester

HRID 854242

反応式

HRID 854242 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:15])[CH:11]=2)[CH:6]=1)=[O:4].[N:16]1([CH2:22][CH2:23][CH2:24]O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:24][CH2:23][CH2:22][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:11]=2)[CH:6]=1)=[O:4]

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 66032Piperidine-1-propanolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 390995Methyl 6-hydroxy-2-naphthoate

生成物 1

HCID 589338936-(3-Piperidin-1-yl-propoxy)-naphthalene-2-carboxylic acid methyl ester収率 76.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 20.2 g (0.1 mol) 6-hydroxy-naphthalene-2-carboxylic acid methyl ester (commercially available), 18.6 g (0.13 mol) 1-piperidinepropanol (commercially available), 50.4 g (0.2 mol) 1,1′-(azodicarbonyl)dipiperidine and 58 ml (0.2 mol) tri-n-butyl-phosphine in 400 ml THF was stirred at room temperature for 16 h. The suspension was filtered off and the filtrate evaoprated to dryness. The residue was taken up in 200 ml DCM and 400 g Isolute® HM-N (Argonaut Technologies Inc., support material for accelerated solvent extraction) was added and evaporated to dryness. The residue was chromatographed over silica eluting with a gradient formed from DCM/MeOH(2N NH3) 99/1 to 9/1. After evaporation the residue was treated with heptan/diethyl ether and the precipitate filtered of and washed again with heptan/diethyl ether. After drying under reduced pressure at 50° C. 25 g (76%) of the title compound was obtained as white solid. MS (m/e): 328.3 (MH+, 100%)

後処理

  1. filtrationThe suspension was filtered off
  2. extraction400 g Isolute® HM-N (Argonaut Technologies Inc., support material for accelerated solvent extraction)
  3. additionwas added
  4. customevaporated to dryness
  5. customThe residue was chromatographed over silica eluting with a gradient
  6. customformed from DCM/MeOH(2N NH3) 99/1 to 9/1
  7. customAfter evaporation the residue
  8. additionwas treated with heptan/diethyl ether
  9. filtrationthe precipitate filtered of and
  10. washwashed again with heptan/diethyl ether
  11. customAfter drying under reduced pressure at 50° C

出典と根拠

ORDレコード
ord-02f4c9ea89154cd09ef829f9f0a3a884
出典データセット
uspto-grants-2007_08
特許番号
US07259158B2

関連ノート

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