Formaldehyde → HCID 57697642, compound

HRID 1524328Notes

Reaction equation

HRID 1524328 reaction equation
[CH3:1][CH:2]1[NH:8][CH2:7][C:6]2[CH:9]=[CH:10][C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[N:12][C:5]=2[O:4][CH2:3]1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:30](C)=O.[Na+].O>C(O)(=O)C.C(Cl)Cl>[CH3:1][CH:2]1[N:8]([CH3:30])[CH2:7][C:6]2[CH:9]=[CH:10][C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:15][CH2:14]3)=[N:12][C:5]=2[O:4][CH2:3]1

Participants

7

Reactant 4

HCID 712Formaldehyde2×HCID 962WaterHCID 5049666Sodium triacetoxyborohydride2×HCID 57697594HCID 57697594, compound

Product 1

HCID 57697642HCID 57697642, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound (0.30 g) obtained in Example 22 and paraformaldehyde (0.052 g) in a mixture of acetic acid (0.20 mL) and CH2Cl2 (4 mL) was added NaBH(OAc)3 (0.274 g), and the mixture was stirred at room temperature for 25 hr. Paraformaldehyde (0.052 g) and NaBH(OAc)3 (0.274 g) were further added, and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into water, and the resultant product was extracted with CH2Cl2. The organic layer was washed with water and brine, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 30→60% ethyl acetate/hexane) to give the title compound (0.122 g, 39%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 days
  2. extractionthe resultant product was extracted with CH2Cl2
  3. washThe organic layer was washed with water and brine
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (solvent gradient; 30→60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e7631138f4db481a85975424774fa152
Source dataset
uspto-grants-2015_07
Patent number
US09079907B2

Reaction notes

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