(4aS,7aS)-tert-butyl 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate → (4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

HRID 2356384Notes

Reaction equation

HRID 2356384 reaction equation
C([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([CH2:11][CH2:12][CH2:13][N:14]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[C:20]([O:19][C:17]([N:14]1[CH2:13][CH2:12][CH2:11][C@@H:10]2[C@H:15]1[CH2:16][NH:8][CH2:9]2)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 1

HCID 29973012(4aS,7aS)-tert-butyl 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

Product 1

HCID 1519435(4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylateYield 86.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The preparation comprises dissolving [1S,6S]-8-benzyl-2-tertbutyloxycarbonyl-2,8-diazabicyclo[4,3,0]nonane (target product of Embodiment 5, 5.0 g, 15.8 mmol) in methanol (50 mL), adding 10% Pd/C (1.0 g) as catalyst for hydrogenation under 3 atm for 10 h, filtering to remove the catalyst, concentrating the filtrate, adding petroleum ether to solidify the product, filtering, and drying obtained filter cake to give [1S,6S]-2-tertbutyloxycarbonyl-2,8-diazabicyclo[4,3,0]nonane(3.1 g, 86.8%), [α]20D=−70.2° (C=4).

Workup

  1. filtrationfiltering
  2. customto remove the catalyst
  3. concentrationconcentrating the filtrate
  4. additionadding petroleum ether
  5. filtrationfiltering
  6. customdrying
  7. customobtained
  8. filtrationfilter cake

Sources & evidence

ORD record
ord-7a144a4c2d294e3cb0d52871b60bf99e
Source dataset
uspto-grants-2010_07
Patent number
US07759362B2

Reaction notes

Loading…