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Azetidine → Tert-Butyl 2-(azetidin-1-ylmethyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

HRID 2388688
Notes
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Reaction equation

HRID 2388688 reaction equation
[CH:1]([C:3]1[S:11][C:10]2[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][C:5]=2[CH:4]=1)=O.[NH:19]1[CH2:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[N:19]1([CH2:1][C:3]2[S:11][C:10]3[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][C:5]=3[CH:4]=2)[CH2:22][CH2:21][CH2:20]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10422AzetidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11845085tert-butyl 2-formyl-4H,5H,6H,7H-thieno[3,2-c]pyridine-5-carboxylate

Product 1

HCID 86635669Tert-Butyl 2-(azetidin-1-ylmethyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

tert-Butyl 2-formyl-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (0.3 g, 0.122 mmol) and azetidine (96 mg, 1.683 mmol) were dissolved in 1,2-dichloro-ethane (7 ml) and stirred at room temperature for 10 min. Sodium triacetoxyboro-hydride (0.331 g, 1.571 mmol) was added and the resulting mixture stirred at room temperature for 48 h. Saturated sodium hydrogen carbonate solution was added and the phases were separated. The aqueous phase was extracted with diethylether (3×) and the organics were washed with saturated sodium chloride solution (1×). The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (ethyl acetate/methanol, 10:1). Yield: 0.28 g (81%).

Workup

  1. stirringthe resulting mixture stirred at room temperature for 48 h
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with diethylether (3×)
  4. washthe organics were washed with saturated sodium chloride solution (1×)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (ethyl acetate/methanol, 10:1)

Sources & evidence

ORD record
ord-3aed17222cba4311bcdba91c40984e02
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08268814B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes