Formaldehyde → HCID 57401546, compound

HRID 902980Notes

Reaction equation

HRID 902980 reaction equation
[C@@H:1]12[CH2:7][NH:6][C@@H:5]1[CH2:4][N:3]([C:8]1[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11](=[O:21])[C:10]=3[CH:9]=1)[CH2:2]2.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:26](C)=O.[Na+]>O>[CH3:26][N:6]1[CH2:7][C@@H:1]2[C@H:5]1[CH2:4][N:3]([C:8]1[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11](=[O:21])[C:10]=3[CH:9]=1)[CH2:2]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67163860HCID 67163860, compound

Product 1

HCID 57401546HCID 57401546, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the product of Example 39B (70 mg, 0.25 mmol) in water (2 mL), was treated with formaldehyde (38% aq., 3 mL) and NaBH(OAc)3 (250 mg, 1.18 mmol; Aldrich). After stirring at room temperature for 60 h, the reaction mixture was concentrated under vacuum and purified by flash chromatography (40 g silica gel, 1:10:89 NH4OH-MeOH-CH2Cl2) to afford the title compound (57 mg, 0.20 mmol; 91% yield): 1H NMR (300 MHz, CD3OD) δ ppm 7.37-7.51 (4H, m), 7.10-7.19 (1H, m), 7.02 (1H, d, J=2 Hz), 6.85 (1H, dd, J=8, 2 Hz), 4.02 (1H, dd, J=6, 5 Hz), 3.72-3.82 (2H, m), 3.15-3.40 (4H, m), 3.03 (1H, dd, J=11, 4 Hz), 2.39 (3H, s); MS (DCl/NH3): m/z 291 (M+1)+.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. custompurified by flash chromatography (40 g silica gel, 1:10:89 NH4OH-MeOH-CH2Cl2)

Sources & evidence

ORD record
ord-b6848b3a93824138af2ed4d14871ed65
Source dataset
uspto-grants-2008_04
Patent number
US07365193B2

Reaction notes

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