2-Bromopyridine → HCID 54396131, compound

HRID 975662Notes

Reaction equation

HRID 975662 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH2:13]([O:16][C:17]([N:19]1[CH2:23][C@H:22]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:21][C@H:20]1[CH:32]=[O:33])=[O:18])[CH:14]=[CH2:15]>O1CCCC1.CCCCCC>[CH2:13]([O:16][C:17]([N:19]1[CH2:23][C@H:22]([O:24][Si:25]([C:28]([CH3:30])([CH3:29])[CH3:31])([CH3:26])[CH3:27])[CH2:21][C@H:20]1[CH:32]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[OH:33])=[O:18])[CH:14]=[CH2:15]

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 22870383(2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-formylpyrrolidineHCID 178418339Butyllithium

Product 1

HCID 54396131HCID 54396131, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2-bromopyridine (21.9 g) in tetrahydrofuran (310 ml) was added dropwise n-butyl lithium (1.65N) in hexane (78 ml) under -60° C. After stirring for 15 minutes, (2S,4R)-1-allyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-formylpyrrolidine (31 g) was added dropwise under -60° C. After stirring for 30 minutes, the reaction mixture was quenched with water and extracted three times with ethyl acetate. The combined organic layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was column chromatographed on silica gel to give 1-{(2S,4R)-1-allyloxycarbonyl-4-(t-butyldimethyl-silyloxy) pyrrolidin-2-yl}-1-(pyridin-2-yl)methanol (13.3 g).

Workup

  1. stirringAfter stirring for 30 minutes
  2. customthe reaction mixture was quenched with water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customchromatographed on silica gel

Sources & evidence

ORD record
ord-19773ebc459344a2a018a210a6ffbbde
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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