Hydrochloric Acid → Methyl 1-((6-hydroxynaphthalen-2-yl)methyl)azetidine-3-carboxylate

HRID 713927

반응식

HRID 713927 반응식
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH2:19][N:20]1[CH2:23][CH:22]([C:24]([O:26][CH3:27])=[O:25])[CH2:21]1)[CH:13]=[CH:12]2)(C(C)(C)C)(C)C.Cl.C([O-])(O)=O.[Na+]>CO>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH2:19][N:20]1[CH2:23][CH:22]([C:24]([O:26][CH3:27])=[O:25])[CH2:21]1)[CH:13]=[CH:12]2

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 66926610Methyl 1-((6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)methyl)azetidine-3-carboxylate

생성물 1

HCID 66925934Methyl 1-((6-hydroxynaphthalen-2-yl)methyl)azetidine-3-carboxylate수율 47.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of methyl 1-((6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)methyl)azetidine-3-carboxylate (4.5 g, 11.7 mmol) in methanol (50 mL) at 0° C. was added con. HCl (5 mL) dropwise. The reaction mixture was stirred at r.t for 1 h. The mixture was neutralized by sat. NaHCO3 and evaporated off most of solvent, extracted with DCM and washed with brine, dried over Na2SO4 and concentrated to obtain crude product. The crude product was purified by silica gel chromatography (DCM:MeOH=40:1), extracted with DCM and washed with brine, dried over Na2SO4 and concentrated to obtain crude product. The crude product was purified by silica gel chromatography (DCM:MeOH=40;1) to give the title compound (1.5 g, 47%) as a gray solid. ESI-MS (M+1)+: 272.0. 1H NMR (400 MHz, CDCl3) δ: 8.14 (s, 1H), 7.59-7.52 (m, 2H), 7.39-7.28 (m, 2H), 7.09-7.04 (m, 2H), 3.92 (s, 2H), 3.86-3.82 (m, 2H), 3.70 (s, 3H), 3.63-3.59 (m, 2H), 3.252-3.46 (m, 1H).

후처리

  1. customevaporated off most of solvent
  2. extractionextracted with DCM
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto obtain crude product
  7. customThe crude product was purified by silica gel chromatography (DCM:MeOH=40:1)
  8. extractionextracted with DCM
  9. washwashed with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated
  12. customto obtain crude product
  13. customThe crude product was purified by silica gel chromatography (DCM:MeOH=40;1)

출처 및 근거

ORD 기록
ord-50d56694ebc34e1bb1616ed03a1f00eb
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09186367B2

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