2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid → HCID 58398107, compound

HRID 2167437Notes

Reaction equation

HRID 2167437 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:18](O)=[O:19])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18][OH:19])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 189883742-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid

Product 1

HCID 58398107HCID 58398107, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.245 mmol of 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid in 2 ml dry THF were added at room temperature 0.736 mmol borane dimethyl sulphide complex and the mixture was stirred over night. The mixture was diluted with EtOAc and washed with saturated Na2CO3 solution and brine. The aqueous layer was extracted with EtOAc. The combined organic layers were washed, dried over MgSO4 and filtered. Evaporation of the solvent gave 60 mg of a pale yellow oil (93%).

Workup

  1. washwashed with saturated Na2CO3 solution and brine
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-67f4c24c680743a2ab5144a96680a492
Source dataset
uspto-grants-2015_06
Patent number
US09045459B2

Reaction notes

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