Sodium cyanoborohydride → HCID 22270721, compound

HRID 1160705Notes

Reaction equation

HRID 1160705 reaction equation
[CH:1]1([CH2:5][O:6][CH:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:8](=O)[CH3:9])[CH2:4][CH2:3][CH2:2]1.[BH3-]C#[N:21].[Na+]>C(Cl)Cl>[NH2:21][CH:8]([CH:7]([O:6][CH2:5][CH:1]1[CH2:4][CH2:3][CH2:2]1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[CH3:9]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 22270328HCID 22270328, compound

Product 1

HCID 22270721HCID 22270721, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-cyclobutylmethoxy-4-(4-chlorophenyl)butan-2-one (247 mg, 0.925 mmol, obtained from Step C) in 0.5 mL CH2Cl2 was added to a stirred suspension of NH4OAc (715 mg, 9.25 mmol) and NaBH3CN (35 mg, 0.555 mmol) at room temperature and allowed to stir overnight. The reaction was quenched by the addition of 2.2 mL conc. HCl allowed to stir for 30 minutes. The solvents were evaporated under reduced pressure and the residue was partitioned between ether and water. The aqueous layer was washed two more times with ether. The combined organics were dried over Na2SO4. The crude product mixture obtained after filtration and removal of volatiles was purified by flash chromatography, eluting using mixtures of mixtures of CH2Cl2 and MeOH (100% CH2Cl2, to 5% MeOH in CH2Cl2) to provide the title compound as a yellow oil, homogeneous by TLC Rf0.12 (5% MeOH in CH2Cl2). 500 MHz 1H NMR (CDCl3): δ 1.16 (t, 3H); 1.67 (m, 2H); 1.85 (m, 3H); 2.01 (m, 2H); 2.48 (m, 1H); 2.74 (m, 2H); 2.90 (dd, 1H); 3.15 (d quint, 2H); 3.37 (m, 2H).

Workup

  1. customThe reaction was quenched by the addition of 2.2 mL conc. HCl
  2. stirringto stir for 30 minutes
  3. customThe solvents were evaporated under reduced pressure
  4. customthe residue was partitioned between ether and water
  5. washThe aqueous layer was washed two more times with ether
  6. dry with materialThe combined organics were dried over Na2SO4
  7. customThe crude product mixture obtained
  8. filtrationafter filtration and removal of volatiles
  9. customwas purified by flash chromatography
  10. washeluting

Sources & evidence

ORD record
ord-2d62e5ddc4814750bfe16e8dd966a6fd
Source dataset
uspto-grants-2010_10
Patent number
US07816534B2

Reaction notes

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