Ammonium Chloride → HCID 66967873, compound

HRID 2377985Notes

Reaction equation

HRID 2377985 reaction equation
[O:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[C:23](=[O:28])N(OC)C)=[O:16])([CH3:13])([CH3:12])[CH3:11].[Cl-].[NH4+]>C1COCC1>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[C:23]([C:2]1[O:1][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1)=[O:28])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 12421098Furo[2,3-b]pyridineHCID 21988510tert-Butyl 2-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

Product 1

HCID 66967873HCID 66967873, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.5N n-Butylithium in hexanes (2.3 ml, 5.75 mmol) was added dropwise over 10 min to a stirred solution of furo[2,3-b]pyridine (0.57 g, 4.79 mmol) (H. Sliwa, Bull. Soc. Chim. France, 646, 1970) in anhydrous THF (20 ml) at −75° C. under argon. The resultant mixture was stirred for 5 min at −70° C. then a solution of (RS)-1-(tert-butyloxycarbonyl)-2-(N-methoxy-N-methylcarbamoyl)-piperidine, D1 (1.41 g, 5.19 mmol) in anhydrous THF (20 ml) was added over 2 min. and the resultant solution stirred at −70° C. for 15 min. The mixture was poured into saturated ammonium chloride (100 ml) and extracted with ethyl acetate (2×50 ml). The combined organics were dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 0-1% ethyl acetate in dichloromethane to give the title compound as a colourless solid (0.51 g, 32%).

Workup

  1. extractionextracted with ethyl acetate (2×50 ml)
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 0-1% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-531bf44bac3b4c6d84e665c4a2ea3c58
Source dataset
uspto-grants-2008_12
Patent number
US07470710B2

Reaction notes

Loading…