Azetidine → HCID 68717531, compound

HRID 1159818Notes

Reaction equation

HRID 1159818 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH:15]1[C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:24]=O)[C:18]=2[CH:17]=[CH:16]1.[NH:26]1[CH2:29][CH2:28][CH2:27]1>C1COCC1.ClCCl.C([O-])(O)=O.[Na+]>[N:26]1([CH2:24][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:18]=2[CH:17]=[CH:16][NH:15]3)[CH2:29][CH2:28][CH2:27]1

Participants

7

Reactant 3

HCID 10422AzetidineHCID 333703Indole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68717531HCID 68717531, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Sodium triacetoxy borohydride (1.46 g, 6.9 mmol) was added to a solution of 1H-indole-4-carbaldehyde (0.5 g, 3.4 mmol) and azetidine (0.39 g, 6.87 mmol) in THF (15 ml). The mixture was stirred for 1 h and diluted with dichloromethane and NaHCO3 (aq). The organic phase was washed with brine (1×), dried (MgSO4) and evaporated. The crude product was dissolved in dichloromethane and hexane was added (1:1). The off white powder was filtered and washed with a mixture of dichloromethane hexane (1:1). Yield: 400 mg (52%). Off white solid. MS (ESI+) for C12H14N2 m/z 187 (M+H)+.

Workup

  1. washThe organic phase was washed with brine (1×)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. dissolutionThe crude product was dissolved in dichloromethane
  5. additionhexane was added (1:1)
  6. filtrationThe off white powder was filtered
  7. washwashed with a mixture of dichloromethane hexane (1:1)

Sources & evidence

ORD record
ord-dba59964aaa34381aab0988dc6c2b05c
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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