Formaldehyde → HCID 11618143, compound

HRID 272298Notes

Reaction equation

HRID 272298 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([N:15]4[CH2:20][CH2:19][CH:18]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=5)[CH2:17][CH2:16]4)=[N:13][N:14]=[C:10]3[CH2:9][NH:8][CH2:7][C:6]=2[CH:27]=1.C=O.[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([N:15]4[CH2:20][CH2:19][CH:18]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=5)[CH2:17][CH2:16]4)=[N:13][N:14]=[C:10]3[CH2:9][N:8]([CH3:30])[CH2:7][C:6]=2[CH:27]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 11559966HCID 11559966, compound

Product 1

HCID 11618143HCID 11618143, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the compound from example 1 (100 mg, 0.26 mmol) in dichloromethane (3 mL) was added formaldehyde (37% aqueous solution, 142 μL, 1.75 mmol) followed by sodium triacetoxyborohydride (55 mg, 0.26 mmol). The solution was stirred for 5 hours at room temperature, then sodium triacetoxyborohydride (20 mg, 0.09 mmol) was added. After 10 minutes, saturated sodium hydrogen carbonate solution was added and the mixture was stirred vigorously for 5 minutes. The phases were separated and the organic phase evaporated in vacuo to give the crude residue which was azeotroped twice with ethyl acetate and then diethyl ether to furnish the desired product, 63 mg (61%) as a white solid.

Workup

  1. waitAfter 10 minutes
  2. stirringthe mixture was stirred vigorously for 5 minutes
  3. customThe phases were separated
  4. customthe organic phase evaporated in vacuo
  5. customto give the crude residue which
  6. customwas azeotroped twice with ethyl acetate

Sources & evidence

ORD record
ord-4d1c4f4024484607b2f28479e297471d
Source dataset
uspto-grants-2008_11
Patent number
US07456170B2

Reaction notes

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