N-BOC-ethylenediamine → HCID 23001280, compound

HRID 398001Notes

Reaction equation

HRID 398001 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]=1C=O.[NH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35].C([BH3-])#N.[Na+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([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[NH:28][CH2:29][CH2:30][NH:31][C:32]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:38]

Participants

5

Reactant 3

HCID 187201N-BOC-ethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 23001298HCID 23001298, compound

Product 1

HCID 23001280HCID 23001280, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 1, Step A (1 eq) and tert-butyl N-(2-aminoethyl)carbamate (3 eq) are dissolved in methanol, to which sodium cyanoborohydride (1.5 eq) is added in portions at 0° C. The reaction is stirred at room temperature until complete, and then 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. The crude product is chromatographed on silica gel with ethyl acetate and hexane to provide the title product.

Workup

  1. additionis added in portions at 0° C
  2. customthen quenched by the addition of saturated aqueous ammonium chloride
  3. stirringstirred until hydrogen evolution ceases
  4. concentrationThe resulting suspension is concentrated in vacuo
  5. custompartitioned between methylene chloride and saturated aqueous sodium bicarbonate
  6. customThe layers are separated
  7. extractionthe aqueous layer is extracted with methylene chloride
  8. dry with materialThe combined organic layers are dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product is chromatographed on silica gel with ethyl acetate and hexane

Sources & evidence

ORD record
ord-7fb9234802c94f88b567ad2c52447702
Source dataset
uspto-grants-2003_08
Patent number
US06610722B2

Reaction notes

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