HCID 15884745, compound → HCID 15884740, compound

HRID 379526Notes

Reaction equation

HRID 379526 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[CH2:14][CH:13]([O:15][CH3:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=O>C1COCC1>[NH2:1][CH2:2][CH2:3][N:5]1[CH2:14][CH:13]([O:15][CH3:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1

Participants

3

Reactant 1

HCID 15884745HCID 15884745, compound

Product 1

HCID 15884740HCID 15884740, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

A solution of N-glycyl-4-methoxy-1,2,3,4-tetrahydroisoquinoline in 25 mL of THF was cooled in an ice bath and 10 M solution of borane-methyl sulfide complex in THF (3.85 mL) was added dropwise. The resulting mixture was warmed to 55° C. and then to reflux for 4 hours. Excess borane was destroyed by addition of 6N HCl. The resulting mixture was heated to 100° C. for 1 hour. The resulting solution was first extracted with EtOAc and then with 10% iPrOH—CH2Cl2. The iPrOH—CH2Cl2 extract gave 880 mg (28%) of the title compound.

Workup

  1. temperatureto reflux for 4 hours
  2. customExcess borane was destroyed by addition of 6N HCl
  3. temperatureThe resulting mixture was heated to 100° C. for 1 hour
  4. extractionThe resulting solution was first extracted with EtOAc
  5. extractionThe iPrOH—CH2Cl2 extract

Sources & evidence

ORD record
ord-c7c89f4633b64a3bb98fc54e8abb3bd9
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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