Sodium cyanoborohydride → HCID 17912344, compound

HRID 586644Notes

Reaction equation

HRID 586644 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]([F:25])([F:24])[C:4]([F:23])([F:22])[C:5]([C:7]1[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[N:13]([C:14]=1[CH3:15])[CH2:12][CH2:11][CH2:10]2)=O.[BH3-]C#N.[Na+]>ClC(Cl)C.[Zn+2].[I-].[I-]>[F:27][C:2]([F:1])([F:26])[C:3]([F:24])([F:25])[C:4]([F:23])([F:22])[CH2:5][C:7]1[C:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:9]2[N:13]([C:14]=1[CH3:15])[CH2:12][CH2:11][CH2:10]2

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydride2×HCID 22335609HCID 22335609, compound

Product 1

HCID 17912344HCID 17912344, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalyst2×HCID 63651,1-DichloroethaneSolvent

Procedure

The solution of 1,1,1,2,2,3,3-heptafluoro-4-(3-methyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-2-yl)-butan-4-one (0.62 g, 1.6 mmol) in dichloroethane (20 ml) is treated successively with NaCNBH3 (0.42 g, 6.4 mmol) and ZnI2 (0.71 g, 2.24 mmol) and refluxed for 4 days (d). After 2 days, NaCNBH3 (0.42 g, 6.4 mmol) and ZnI2 (0.71 g, 2.24 mmol) are again added. The reaction is observed by means of GC-MS. After 2 days, 40% of the compound employed is reacted, and after 4 days 89%, in addition to a further 11% of starting material. The reaction is then terminated by addition of dilute phoshoric acid (8%, 50 ml). After the evolution of gas has ended, the mixture is extracted with methylene chloride, the organic phase is washed with water (50 ml) and the solvent is stripped off in vacuo after drying over Na2SO4 sicc. The residue (0.65 g, 82.4%, 77% strength according to GC-MS(TIC)) is employed in the subsequent reaction without further purification.

Workup

  1. temperaturerefluxed for 4 days (d)
  2. waitAfter 2 days
  3. waitafter 4 days 89%
  4. customThe reaction is then terminated by addition of dilute phoshoric acid (8%, 50 ml)
  5. extractionthe mixture is extracted with methylene chloride
  6. washthe organic phase is washed with water (50 ml)
  7. dry with materialafter drying over Na2SO4 sicc
  8. customThe residue (0.65 g, 82.4%, 77% strength according to GC-MS(TIC)) is employed in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-2699249186f24738876723fceaa020b7
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

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