Sodium borohydride → HCID 58661629, compound

HRID 1487011Notes

Reaction equation

HRID 1487011 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([F:20])([C:18]#[N:19])[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.[BH4-].[Na+]>CO.Cl[Ni]Cl>[CH:1]([N:14]1[CH2:15][C:16]([CH2:18][NH2:19])([F:20])[CH2:17]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 2

HCID 4311764Sodium borohydrideHCID 58661631HCID 58661631, compound

Product 1

HCID 58661629HCID 58661629, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

1-Benzhydryl-3-fluoroazetidine-3-carbonitrile (0.5 g, 1.88 mmol) was dissolved in methanol (25 mL). NaBH4 (0.49 g, 13.14 mmol) and NiCl2 (0.044 g, 0.34 mmol) were added at 0° C. and the reaction mixture was stirred at rt for 14 h. The solids formed were removed by filtration and the filtrate was concentrated under reduced pressure. The crude product was purified by chromatography (0-5% methanol-DCM) to give 0.15 g of (1-benzhydryl-3-fluoroazetidin-3-yl)methanamine (30% yield). 1H NMR (400 MHz, CDCl3, ppm) δ=7.46-7.19 (m, 10H); 4.48 (s, 1H); 3.38-3.34 (t, 2H); 3.26-3.09 (m, 4H).

Workup

  1. customThe solids formed
  2. customwere removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude product was purified by chromatography (0-5% methanol-DCM)

Sources & evidence

ORD record
ord-2149e695473c4be491107b4eb80da905
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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