Sodium hydrido[tris(methanolato)]borate(1-) → HCID 18440784, compound

HRID 457902Notes

Reaction equation

HRID 457902 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[N:14]=[C:15]([C:24]([CH3:28])([CH3:27])[CH2:25][NH2:26])[NH:16][C:17]=1[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)[CH:7]=[CH:6]2.CO[BH-](OC)OC.[Na+]>ClCCl.O>[CH:5]1([CH2:6][NH:26][CH2:25][C:24]([C:15]2[NH:16][C:17]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:13]([C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:9]=3)[N:14]=2)([CH3:28])[CH3:27])[CH2:10][CH2:11][CH2:12][CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 3084262Sodium hydrido[tris(methanolato)]borate(1-)HCID 18440775HCID 18440775, compound

Product 1

HCID 18440784HCID 18440784, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Example 2 (20 mg, 0.05 mmol) in dichloromethane (2 mL) was treated with cyclohexaldehyde (3 mg, 0.07 mmol) and sodium trimethoxyborohydride (9 mg, 0.07 mmol). The solution was stirred at room temperature for 4 hours. The mixture was diluted with water and extracted with ethyl acetate. The aqueous layer was separated and extracted with additional ethyl acetate, the organic layers were combined, dried over anhydrous magnesium sulphate, filtered and concentrated at reduced pressure. The residue was chromatographed on a Gilson HPLC to give the title compound (10 mg, 40%) as a yellow solid; MS(ES) m/e 469 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe aqueous layer was separated
  3. extractionextracted with additional ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was chromatographed on a Gilson HPLC

Sources & evidence

ORD record
ord-f156611ac9ad4424be1e86b01db296c5
Source dataset
uspto-grants-2007_03
Patent number
US07189745B1

Reaction notes

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