Veratraldehyde → HCID 86638159, compound

HRID 423416Notes

Reaction equation

HRID 423416 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH:11]([NH:13][CH3:14])[CH:10]([OH:15])[CH2:9]2)=[N:6][CH:7]=1.[CH:16](=O)[C:17]1[CH:26]=[CH:25][C:22]([O:23][CH3:24])=[C:19]([O:20][CH3:21])[CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(=O)(O)[O-].[Na+].C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][C@@H:11]([N:13]([CH2:16][C:17]3[CH:26]=[CH:25][C:22]([O:23][CH3:24])=[C:19]([O:20][CH3:21])[CH:18]=3)[CH3:14])[C@H:10]([OH:15])[CH2:9]2)=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 8419VeratraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66673284HCID 66673284, compound

Product 1

HCID 86638159HCID 86638159, compoundYield 72.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 63651,1-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Dissolve 1-(5-bromo-pyridin-2-yl)-4-methylamino-pyrrolidin-3-ol (0.347 g, 1.28 mmol) in dichloroethane (10 mL) and add veratraldehyde (212 mg, 1.28 mmol), sodium triacetoxyborohydride (405 mg, 1.91 mmol) and acetic acid (125 mL, 2.18 μmol). Stir the mixture at room temperature overnight. Dilute with saturated sodium bicarbonate and extract the mixture with dichloromethane (3×). Dry the combined organic portions over sodium sulfate, filter, and evaporate. Purify the resulting residue by silica gel chromatography, eluting with 0-9% methanol (2N NH3)/CH2Cl2 to give 390 mg (72%) of the title compound as a white solid. MS/ES m/z (81Br) 424.0 [M+H]+.

Workup

  1. extractionextract the mixture with dichloromethane (3×)
  2. dry with materialDry the combined organic portions over sodium sulfate
  3. filtrationfilter
  4. customevaporate
  5. customPurify the resulting residue by silica gel chromatography
  6. washeluting with 0-9% methanol (2N NH3)/CH2Cl2

Sources & evidence

ORD record
ord-0ecfa22d2c5046a4904bc2595f333246
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

Loading…