1-Bromo-3-chloropropane → HCID 86729492, compound

HRID 712456Notes

Reaction equation

HRID 712456 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]2[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][CH:2]12.Br[CH2:18][CH2:19][CH2:20][Cl:21].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:21][CH2:20][CH2:19][CH2:18][N:1]1[CH2:6][CH2:5][CH2:4][CH:3]2[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][CH:2]12

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 68729079tert-Butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate

Product 1

HCID 86729492HCID 86729492, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of tert-butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate (1.60 g), 1-bromo-3-chloropropane (1.50 mL) and K2CO3 (3.00 g) in acetone was heated to reflux for 9 h. The reaction mixture was cooled to rt and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 1:1 (v/v) PE/EA) to give the title compound as yellow oil (0.53 g, 65.00%), HPLC: 89.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 303.2 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 9 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was chromatographed with a silica gel column (eluting agent: 1:1 (v/v) PE/EA)

Sources & evidence

ORD record
ord-4ef43fb5bf40426285fc703b67dd911d
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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