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

HRID 2404147

Reaction equation

HRID 2404147 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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), 3.52-3.46 (m, 1H).

Workup

  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)

Sources & evidence

ORD record
ord-d368c7d099e44e71b33cb7d62227a397
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Linked notes

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