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

HRID 854242

반응식

HRID 854242 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-02f4c9ea89154cd09ef829f9f0a3a884
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259158B2

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