Sodium cyanoborohydride → HCID 23001283, compound

HRID 397995Notes

Reaction equation

HRID 397995 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:3]=1[CH:4]=O.C([BH3-])#[N:29].[Na+]>CO.C([O-])(=O)C.[NH4+]>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][Si:11]([C:24]([CH3:25])([CH3:26])[CH3:27])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:6][C:3]=1[CH2:4][NH2:29]

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 23001298HCID 23001298, compound

Product 1

HCID 23001283HCID 23001283, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 517165Ammonium AcetateSolvent

Procedure

The product from Step A is dissolved in methanol saturated with ammonium acetate. Sodium cyanoborohydride is added in portions at 0° C., and the reaction stirred at room temperature until complete. The reaction is quenched by the addition of saturated aqueous ammonium chloride and stirred until hydrogen evolution ceases. The resulting suspension is concentrated in vacuo and then partitioned between methylene chloride and saturated aqueous sodium bicarbonate. The layers are separated and the aqueous layer is extracted with methylene chloride. The combined organic layers are dried over sodium sulfate, filtered, and concentrated in vacuo to provide the title product.

Workup

  1. customThe reaction is quenched by the addition of saturated aqueous ammonium chloride
  2. stirringstirred until hydrogen evolution ceases
  3. concentrationThe resulting suspension is concentrated in vacuo
  4. custompartitioned between methylene chloride and saturated aqueous sodium bicarbonate
  5. customThe layers are separated
  6. extractionthe aqueous layer is extracted with methylene chloride
  7. dry with materialThe combined organic layers are dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-582492e67b524f238810c7f55e3f9699
Source dataset
uspto-grants-2003_08
Patent number
US06610722B2

Reaction notes

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