Sodium Bicarbonate → HCID 57679184, compound

HRID 492152Notes

Reaction equation

HRID 492152 reaction equation
[CH3:1][N:2]([CH2:10][C:11]1([CH2:20][CH:21]=O)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[C@@H:23]12[NH:30][C@@H:27]([CH2:28][CH2:29]1)[CH2:26][CH:25]([N:31]1[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[N:33]=[C:32]1[CH3:40])[CH2:24]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH3:1][N:2]([CH2:10][C:11]1([CH2:20][CH2:21][N:30]2[C@H:27]3[CH2:28][CH2:29][C@@H:23]2[CH2:24][CH:25]([N:31]2[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[N:33]=[C:32]2[CH3:40])[CH2:26]3)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 28467440HCID 28467440, compoundHCID 57679172HCID 57679172, compound

Product 1

HCID 57679184HCID 57679184, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

tert-butyl methyl{[1-(2-oxoethyl)-2,3-dihydro-1H-inden-1-yl]methyl}carbamate (600 mg, 1.98 mmole) and 1-[(1R,5S)-8-azabicyclo[3.2.1]oct-3-yl]-2-methyl-1H-benzimidazole (622 mg, 1.98 mmole) was dissolved in 50 ml of DCE to which was added sodium triacetoxyborohydride (839 mg, 3.96 mmole) which was stirred overnight. A saturated solution of NaHCO3 was added to quench the remaining hydride. The organic layer was washed with water and evaporated. The resulting residue was absorbed into silica gel and 100% EtOAc was use to remove impurities followed by Methanol to remove the product affording 0.7425 g of tert-butyl methyl[(1-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-2,3-dihydro-1H-inden-1-yl)methyl]carbamate (70% yield).

Workup

  1. customto quench the remaining hydride
  2. washThe organic layer was washed with water
  3. customevaporated
  4. customThe resulting residue was absorbed into silica gel and 100% EtOAc
  5. customto remove impurities
  6. customto remove the product

Sources & evidence

ORD record
ord-6df6f4bc2c684d5faa4f315523914bf3
Source dataset
uspto-grants-2009_05
Patent number
US07531661B2

Reaction notes

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