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 8732Notes

Reaction equation

HRID 8732 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-0008c02400784d04915e7583d17b8539
Source dataset
uspto-grants-2006_08
Patent number
US07091200B2

Reaction notes

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