Acetic Acid → tert-Butyl octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

HRID 1428249Notes

Reaction equation

HRID 1428249 reaction equation
[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CC(O)=O>CCOC(C)=O.[Pt](=O)=O>[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:9]2[CH:4]([NH:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59566510HCID 59566510, compound

Product 1

HCID 66823462tert-Butyl octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

The product of Step 3 (2.66 g, 12.2 mmol) was added to a Parr shaker pressure vessel that was subsequently purged with nitrogen. Platinum (IV) oxide (0.277 g, 1.22 mmol) was added, followed by AcOH (27 mL). The vessel was placed on a Parr shaker apparatus and was sealed and evacuated and refilled with nitrogen 4 times (with shaking in between cycles). The vessel was then evacuated and refilled with hydrogen 4 times (with shaking in between cycles). The reaction was shaken under hydrogen pressure (approximately 60 psi; the vessel was recharged up to 60 psi as needed) for 48 hours. An additional amount of platinum (IV) oxide (0.277 g, 1.22 mmol) was added in order to drive the reaction to completion. After 24 hours, the reaction mixture was diluted with EtOAc (50 mL) and filtered through a Celite cartridge (Celite 545 Isolute®SPE column; Biotage, Inc.), rinsing the filter cake with additional EtOAc. The filtrate was concentrated in vacuo to a crude oil which was azeotroped with heptane several times until a constant weight was achieved, affording the desired product (HOAc salt). LRMS calc'd for C12H23N2O2 [M+H]+, 227; found 227.

Workup

  1. customwas subsequently purged with nitrogen
  2. customwas sealed
  3. customevacuated
  4. additionrefilled with nitrogen 4 times (with shaking in between cycles)
  5. customThe vessel was then evacuated
  6. additionrefilled with hydrogen 4 times (with shaking in between cycles)
  7. customfor 48 hours
  8. customthe reaction to completion
  9. filtrationfiltered through a Celite cartridge (Celite 545 Isolute®SPE column; Biotage, Inc.)
  10. washrinsing the filter cake with additional EtOAc
  11. concentrationThe filtrate was concentrated in vacuo to a crude oil which
  12. customwas azeotroped with heptane several times until a constant weight

Sources & evidence

ORD record
ord-e0ccfc61b8874e209156c020f0937118
Source dataset
uspto-grants-2015_01
Patent number
US08937077B2

Reaction notes

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