Butanal → HCID 178448434, compound

HRID 849428Notes

Reaction equation

HRID 849428 reaction equation
[ClH:1].Cl.Cl.C([C:6]1[CH:7]=[CH:8][C:9]2[N:15]([CH2:16][C:17]3[N:18]=[CH:19][NH:20][CH:21]=3)[CH2:14][C@@H:13]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:12][CH2:11][C:10]=2[CH:29]=1)#N.[CH:30](=O)[CH2:31][CH2:32][CH3:33].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.C(Cl)Cl>[ClH:1].[ClH:1].[ClH:1].[CH2:30]([N:12]1[CH2:11][C:10]2[CH:29]=[CH:6][CH:7]=[CH:8][C:9]=2[N:15]([CH2:16][C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)[CH2:14][CH:13]1[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 261ButanalHCID 5049666Sodium triacetoxyborohydrideHCID 178478582HCID 178478582, compound

Product 1

HCID 178448434HCID 178448434, compoundYield 354.3%

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

A solution of Example 391 (0.23 g, 0.7 mmol) and butyraldehyde (1 g, 14 mmol) in 1:4 AcOH/CH2Cl2 (25 mL) was stirred at rt for 1 hr. NaBH(OAc)3 (3.0 g, 14 mmol) was added and stirring was continued for 14 hrs. The reaction was quenched with conc. NH4OH and diluted with 10% iPrOH in CH2Cl2 (50 mL). The organic phase was washed with 1 N NaOH (2×20 mL), dried over Na2SO4 and evaporated to give a yellow solid (0.4 g) which was purified by reverse phase preparative HPLC (gradient of aqueous methanol with 0.1% TFA) and converted to the HCl salt by lyophilizing with 1 N HCl to give Example 392 as a yellow solid (45 mg, 12%). MS (M+H)+ 400.

Workup

  1. customThe reaction was quenched with conc. NH4OH
  2. additiondiluted with 10% iPrOH in CH2Cl2 (50 mL)
  3. washThe organic phase was washed with 1 N NaOH (2×20 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-4fd91a5899f54ef4a32b11839b2ab877
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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