5-(imino-morpholin-4-yl-methyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester → 5-(imino-morpholin-4-yl-methyl)-3,4-dihydro-1H-isoquinoline

HRID 2183716Notes

Reaction equation

HRID 2183716 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:18](=[NH:25])[N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[NH:25]=[C:18]([N:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1)[C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH2:16][CH2:17][NH:8][CH2:9]2

Participants

4

Reactant 1

HCID 695955285-(imino-morpholin-4-yl-methyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 219836115-(imino-morpholin-4-yl-methyl)-3,4-dihydro-1H-isoquinolineYield 105.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

5-(Imino-morpholin-4-yl-methyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 27a (0.24 g, 0.69 mmol) was dissolved to room temperature in 10 mL of 10% trifluoroacetic acid in dichloromethane and stirred to room temperature for 18 h. The volatiles were evaporated, the residue was suspended in toluene and evaporated again. The residue was purified by flash chromatography eluting with 7% methanol in dichloromethane containing 0.7% of ammonium hydroxide to yield 0.179 g of 5-(imino-morpholin-4-yl-methyl)-3,4-dihydro-1H-isoquinoline 28a.

Workup

  1. customThe volatiles were evaporated
  2. customevaporated again
  3. customThe residue was purified by flash chromatography
  4. washeluting with 7% methanol in dichloromethane containing 0.7% of ammonium hydroxide

Sources & evidence

ORD record
ord-994d6f14a21648adb61fab2f8245b439
Source dataset
uspto-grants-2005_05
Patent number
US06900220B2

Reaction notes

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