Formaldehyde → HCID 11381163, compound

HRID 553030Notes

Reaction equation

HRID 553030 reaction equation
[CH:1]12[CH2:8][NH:7][CH2:6][CH:5]1[CH2:4][N:3]([C:9]1[CH:21]=[CH:20][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12](=[O:22])[C:11]=3[CH:10]=1)[CH2:2]2.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:27](C)=O.[Na+]>>[CH3:27][N:7]1[CH2:8][CH:1]2[CH:5]([CH2:4][N:3]([C:9]3[CH:21]=[CH:20][C:19]4[C:18]5[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=5)[C:12](=[O:22])[C:11]=4[CH:10]=3)[CH2:2]2)[CH2:6]1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11208526HCID 11208526, compound

Product 1

HCID 11381163HCID 11381163, compoundYield 100%

Procedure

The product of Example 13B (130 mg, 0.46 mmol) was treated with aqueous formaldehyde (5 mL, 37%; EM Science) and NaBH(OAc)3 (163 mg, 0.77 mmol; Aldrich). After stirring for 3 h, the reaction was quenched with saturated NaHCO3 (5 mL) and diluted with CH2Cl2 (5 mL). The layers were separated and the aqueous phase was extracted with CH2Cl2 (3×5 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure and purified via column chromatography (silica gel, 1:9:90 NH4OH/CH3OH/CH2Cl2) to give the title compound (>100%, impure). MS (DCI/NH3) m/z 305 (M+H)+.

Workup

  1. customthe reaction was quenched with saturated NaHCO3 (5 mL)
  2. additiondiluted with CH2Cl2 (5 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (3×5 mL)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified via column chromatography (silica gel, 1:9:90 NH4OH/CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-686f912a89c44e44b638d88557741ea0
Source dataset
uspto-grants-2011_05
Patent number
US07951791B2

Reaction notes

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