Water → HCID 66755141, compound

HRID 2387940Notes

Reaction equation

HRID 2387940 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Li]CCCC.[O:13]=[C:14]1[CH2:31][CH2:30][C:17]2([CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[CH2:16][CH2:15]1.O>CCOCC>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][C:17]2([CH2:30][CH2:31][C:14]([OH:13])([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)[CH2:15][CH2:16]2)[CH2:18][CH2:19]1)=[O:24])([CH3:27])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 122863-BromopyridineHCID 51072194tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylateHCID 178418339Butyllithium

Product 1

HCID 66755141HCID 66755141, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3-Bromopyridine (14.9 mmol, 1 equiv.) was dissolved in ether (50 ml) and added dropwise at −78° C. to a solution of n-BuLi (16.5 mmol, 1.17 M solution in ether, 1.1 equiv.). The mixture was stirred for 20 minutes. tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (stage (iv) Amine F-40) (7.49 mmol) was then dissolved in ether (90 ml) and added slowly. The reaction mixture was stirred for a further hour at −78° C. Distilled water was added and the mixture was thawed to 25° C. The phases were separated, and the organic phase was washed with saturated NaCl solution (30 ml), dried over Na2SO4 and concentrated. The crude product was taken up in ethyl acetate (10 ml) and a solid was precipitated with hexane (30 ml). The solid was filtered off and dried under a high vacuum to yield the desired product. Yield: 50%

Workup

  1. additionadded slowly
  2. stirringThe reaction mixture was stirred for a further hour at −78° C
  3. customwas thawed to 25° C
  4. customThe phases were separated
  5. washthe organic phase was washed with saturated NaCl solution (30 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customa solid was precipitated with hexane (30 ml)
  9. filtrationThe solid was filtered off
  10. customdried under a high vacuum

Sources & evidence

ORD record
ord-6038442455bd438db80d392547500dec
Source dataset
uspto-grants-2012_09
Patent number
US08269000B2

Reaction notes

Loading…