Sodium cyanoborohydride → HCID 18947587, compound

HRID 1590730Notes

Reaction equation

HRID 1590730 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH:9]=2)[C:4]([C:21](=O)[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:3]1[CH2:30][C:31]([CH3:37])([CH3:36])[C:32]([O:34][CH3:35])=[O:33].[BH3-]C#N.[Na+]>ClCCCl.[Zn+2].[I-].[I-]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH:9]=2)[C:4]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:3]1[CH2:30][C:31]([CH3:37])([CH3:36])[C:32]([O:34][CH3:35])=[O:33]

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 18947583HCID 18947583, compound

Product 1

HCID 18947587HCID 18947587, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 500 mg of the benzoyl derivative from Step D of Example 24 in 10 mL of 1,2-dichloroethane were added 1.19 g of ZnI2 and 700 mg of NaBH3CN. The mixture was heated at 65° C. for 5 hours and cooled to R.T. The mixture was quenched with 1N aq. HCl and extracted with CH2Cl2. The extracts were washed with brine, dried over Na2SO4 and evaporated to dryness to give an oil which was chromatographed on flash silica gel using ethyl acetate:hexane (15:85) as eluant to isolate the title compound as a white foam.

Workup

  1. temperaturecooled to R.T
  2. customThe mixture was quenched with 1N aq. HCl
  3. extractionextracted with CH2Cl2
  4. washThe extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customto give an oil which
  8. customwas chromatographed on flash silica gel

Sources & evidence

ORD record
ord-f27514d510134787972fc5a8add5c2ec
Source dataset
uspto-grants-1993_04
Patent number
US05204344

Reaction notes

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