Tert.butyl 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxamide → Tert.butyl 1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxamide

HRID 742872Notes

Reaction equation

HRID 742872 reaction equation
[C:1]([C:5]1([C:28]([NH2:30])=[O:29])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH2:8][CH2:7][N:6]1C(OCC1C=CC=CC=1)=O)=[CH:16][CH:15]=[CH:14][CH:13]=3)([CH3:4])([CH3:3])[CH3:2]>Br.C(O)(=O)C>[C:1]([C:5]1([C:28]([NH2:30])=[O:29])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH2:8][CH2:7][NH:6]1)=[CH:16][CH:15]=[CH:14][CH:13]=3)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86746252Tert.butyl 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxamide

Product 1

HCID 86746253Tert.butyl 1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxamideYield 77.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

1.62 g of tert.butyl 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxamide were dissolved in 10 ml of a 45% solution of hydrogen bromide in acetic acid. After 30 minutes the solution was evaporated and the residue was taken up in water. After filtration the filtrate was washed three times with diethyl ether and then neutralized by the addition of saturated aqueous sodium bicarbonate solution. The product was extracted from the now turbid aqueous layer with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulphate and evaporated to give 0.84 g of tert.butyl 1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxamide as a white crystalline solid of melting point 144° C.

Workup

  1. customAfter 30 minutes the solution was evaporated
  2. filtrationAfter filtration the filtrate
  3. washwas washed three times with diethyl ether
  4. additionneutralized by the addition of saturated aqueous sodium bicarbonate solution
  5. extractionThe product was extracted from the now turbid aqueous layer with ethyl acetate
  6. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-79ea7faf46dd438f8a7607c920cf157e
Source dataset
uspto-grants-1996_09
Patent number
US05554756

Reaction notes

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