Formaldehyde → HCID 122504704, compound

HRID 1487019Notes

Reaction equation

HRID 1487019 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([CH2:19]N)([F:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]=O.[BH3-][C:24]#[N:25].[Na+]>CO>[CH:1]([N:14]1[CH2:17][C:16]([CH2:19][N:25]([CH3:24])[CH3:21])([F:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58661629HCID 58661629, compound

Product 1

HCID 122504704HCID 122504704, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1-Benzhydryl-3-fluoroazetidin-3-yl)methanamine (0.5 g, 1.0 eq.) was dissolved in methanol and HCHO (0.138 g, 2.5 eq.) and NaCNBH3 (0.47 g, 4.0 eq.) were added at 0° C. The reaction mixture was stirred for 14 h at room temperature, then quenched with aqueous ammonium chloride solution and extracted with DCM. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to afford 150 mg of 1-(1-benzhydryl-3-fluoroazetidin-3-yl)-N,N-dimethylmethanamine (100%), which was used in the next step without further purification.

Workup

  1. customquenched with aqueous ammonium chloride solution
  2. extractionextracted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c2f51e880ac4d06aea1a9b98eac7a62
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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