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Product Details of tert-Butyl hexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate

CAS No. :885270-57-5
Formula : C12H22N2O2
M.W : 226.32
SMILES Code : CC(C)(C)OC(=O)N1CC2CCNCC2C1
MDL No. :MFCD08234697
InChI Key :CQJSNQCNXVJXDM-UHFFFAOYSA-N
Pubchem ID :23282882

Safety of tert-Butyl hexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280

Application In Synthesis of tert-Butyl hexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 885270-57-5 ]

[ 885270-57-5 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 885270-57-5 ]
  • [ 100-39-0 ]
  • [ 1114985-10-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;18-crown-6 ether; In tetrahydrofuran; at 20℃; for 16.0h; 34.1 tert-butyl 5-benzylhexahydro-1 H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate0.777 g of benzylbromide (4.54 mmol) were added dropwise to a mixture of 1.028 g of of commercially available tert-butyl hexahydro-1 H-pyrrolo[3,4-c]pyridine-2(3H)- carboxylate (4.54 mmol), 1.883 g potassium carbonate (13.62 mmol) and a spatula tip of 18-crown-6 in 25 ml of tetrahydrofurane. The reaction mixture was stirred for 16 h at room temperature, filtered and the filtrate was concentrated. The residue was dissolved in dichloromethane, the organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated to yield 1.413 g of product that was used in the subsequent step without further purification. MS (ESI+) m/z = 317.2 [M+H]+
  • 2
  • tert-butyl 6-oxohexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)carboxylate [ No CAS ]
  • [ 885270-57-5 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; In tetrahydrofuran; at -10 - 20℃; for 3.0h; To a solution of tert-butyl 6-oxohexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate 15e (600 mg, 2.5 mmol) in 20 mL THF was added a solution of LiAlH4 (190 mg, 50 mmol) in 10 mL THF at -10 C. The resulting mixture was stirred at room temperature for 3 h. To the reaction mixture was added 0.19 mL water, 0.19 mL 15% aq. NaOH and 0.51 mL water in sequence, then the mixture was allowed to stir for another 30 min and filtered. The filtrate was concentrated under reduced pressure to give tert-butyl hexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate 15d as yellow oil which was used directly without purification.
  • 3
  • [ 148404-28-8 ]
  • [ 885270-57-5 ]
  • 4
  • hexahydro-1H-pyrrolo[3,4-c]pyridin-6(2H)one [ No CAS ]
  • [ 885270-57-5 ]
  • 5
  • [ 885270-57-5 ]
  • tert-butyl-5-nitrosohexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylic ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; sodium nitrite; In water; at 0 - 25℃; for 2.0h; Step 1: a water solution (10.00 mL) of sodium nitrite (420.00 mg, 6.09 umol) was dropwise added to a mixed solution of acetic acid (10.00 mL) and water (10.00 mL) of <strong>[885270-57-5]tert-butylhexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylic ester</strong> (800.00 mg, 3.04 umol) at 0C. After the sodium nitrite solution was added, the mixture was warmed up to 25C and stirred for 2 h. TLC showed that the raw materials were consumed. The reaction solution was diluted by water (20 mL) and extracted by ethyl acetate (30 mL*2). Merged organic layers were adjusted by saturated sodium dicarbonate to pH=8-9, washed by saline solution (10 mL*2), dried by anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain tert-butyl-5-nitrosohexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylic ester (650.00 mg, crude product) which was yellow oily matter. The product was directly used in next step without needing further purification. The value of C12H21N3O3[M+H]+256 was calculated using MS ESI, and was 256.
  • 6
  • [ 885270-57-5 ]
  • tert-butyl-5-aminohexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylic ester [ No CAS ]
  • 7
  • [ 885270-57-5 ]
  • tert-butyl 5-[7-(tosyl)pyrrolo[2,3-d]pyrimidin-4-yl]aminohexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylic ester [ No CAS ]
  • 8
  • [ 885270-57-5 ]
  • N-hexahydro-1H-pyrrolo[3,4-c]pyridin-5(6H)-yl-7-(tosyl)7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]
  • 9
  • [ 885270-57-5 ]
  • N-hexahydro-1H-pyrrolo[3,4-c]pyridin-5(6H)-yl-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]
  • 10
  • [ 885270-57-5 ]
  • 3-[5-((7H)-pyrrolo[2,3-d]pyrimidin-4-ylamino)hexahydro-1H-pyrrolo[3,4-c]pyridine-2-yl]oxopropanenitrile [ No CAS ]
 

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