Formaldehyde → HCID 21925543, compound

HRID 1243593Notes

Reaction equation

HRID 1243593 reaction equation
C=O.[C:3](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:17][C:18]1[CH:48]=[CH:47][C:21]2[N:22]3[C:26]([CH2:27][N:28]([CH:30]4[CH2:34][CH2:33][NH:32][CH2:31]4)[CH2:29][C:20]=2[CH:19]=1)=[N:25][N:24]=[C:23]3[CH:35]1[CH2:40][CH2:39][N:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[CH2:37][CH2:36]1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:17][C:18]1[CH:48]=[CH:47][C:21]2[N:22]3[C:26]([CH2:27][N:28]([CH:30]4[CH2:34][CH2:33][N:32]([CH3:3])[CH2:31]4)[CH2:29][C:20]=2[CH:19]=1)=[N:25][N:24]=[C:23]3[CH:35]1[CH2:36][CH2:37][N:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21925632HCID 21925632, compound

Product 1

HCID 21925543HCID 21925543, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formaldehyde (18 μl, 37 wt. % solution in water, 0.22 mmol) and sodium triacetoxyborohydride (47 mg, 0.22 mmol) were added to a solution of the amine from example 56 (100 mg, 0.22 mmol) in dichloromethane (5 ml), and the reaction mixture was stirred at room temperature for 30 minutes. Saturated aqueous sodium bicarbonate solution (10 ml) was added, the mixture was stirred vigorously for 10 minutes, and the layers were separated. The organic layer was evaporated under reduced pressure and the residue purified by column chromatography on silica gel using dichloromethane:methanol: 0.88 ammonia (95:5:0.5) as eluant. The product was azeotroped with ether to afford the title compound (60 mg).

Workup

  1. stirringthe mixture was stirred vigorously for 10 minutes
  2. customthe layers were separated
  3. customThe organic layer was evaporated under reduced pressure
  4. customthe residue purified by column chromatography on silica gel
  5. customThe product was azeotroped with ether

Sources & evidence

ORD record
ord-4571497ea794406b93cdf92b2a6dc4d1
Source dataset
uspto-grants-2006_10
Patent number
US07119088B2

Reaction notes

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