1-Bromo-3-chloropropane → tert-butyl5-(3-chloropropyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

HRID 712430Notes

Reaction equation

HRID 712430 reaction equation
[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:9]2[CH:4]([CH2:5][NH:6][CH2:7][CH2:8]2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH2:26][Cl:27]>CC(C)=O.O>[C:13]([O:12][C:10]([N:1]1[CH:9]2[CH:4]([CH2:5][N:6]([CH2:24][CH2:25][CH2:26][Cl:27])[CH2:7][CH2:8]2)[CH2:3][CH2:2]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 49761056(3aR,7aS)-rel-tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Product 1

HCID 86729480tert-butyl5-(3-chloropropyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylateYield 77%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (0.63 g) in acetone (15 mL) was added K2CO3 (1.54 g) and 1-bromo-3-chloropropane (1.45 mL). The reaction mixture was heated to reflux overnight, diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH) to give the title compound as pale yellow liquid (0.65 g, 77.00%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4 for 1 h
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-c5852cc59b004a03a9ae3186471a89ae
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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