Formaldehyde → HCID 21925586, compound

HRID 2118024Notes

Reaction equation

HRID 2118024 reaction equation
C=O.[N:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:8][CH2:7][CH:6]([C:9]2[N:18]3[C:12]([CH2:13][NH:14][CH2:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=43)=[N:11][N:10]=2)[CH2:5][CH2:4]1.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:29][N:14]1[CH2:13][C:12]2[N:18]([C:9]([CH:6]3[CH2:7][CH2:8][N:3]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[CH2:4][CH2:5]3)=[N:10][N:11]=2)[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[CH2:15]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11961325HCID 11961325, compound

Product 1

HCID 21925586HCID 21925586, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formaldehyde (37% w/v aqueous, 1 ml, 81 mmol) was added to a solution of the amine of example 1 (100 mg, 0.28 mmol) in dichloromethane (20 ml). The mixture was stirred at room temperature for 0.25 hours before sodium triacetoxyborohydride (500 mg, 2.4 mmol) was added. The reaction mixture was stirred for a further 0.25 hours. The dichloromethane was removed under reduced pressure. The residue was partitioned between 2N aqueous sodium hydroxide solution (50 ml) and ethyl acetate (50 ml). The organic layer was washed with saturated brine and dried over magnesium sulphate before filtering and evaporating the filtrate under reduced pressure to give the title compound as a pale yellow foam (75 mg)

Workup

  1. additionwas added
  2. customThe dichloromethane was removed under reduced pressure
  3. customThe residue was partitioned between 2N aqueous sodium hydroxide solution (50 ml) and ethyl acetate (50 ml)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationbefore filtering
  7. customevaporating the filtrate under reduced pressure

Sources & evidence

ORD record
ord-754289401893424a80a3b1878526ae6f
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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