Potassium Hydroxide → HCID 21919474, compound

HRID 1244686Notes

Reaction equation

HRID 1244686 reaction equation
[OH-].[K+].C([O:5][C:6]([CH:8]1[CH2:25][N:12]2[CH2:13][CH2:14][C:15]3[C:20]([CH:11]2[CH2:10][CH:9]1[NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)=[O:7])C>O1CCCC1.O>[C:30]([O:29][C:27]([NH:26][CH:9]1[CH:8]([C:6]([OH:7])=[O:5])[CH2:25][N:12]2[CH2:13][CH2:14][C:15]3[C:20]([CH:11]2[CH2:10]1)=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 66692096HCID 66692096, compound

Product 1

HCID 21919474HCID 21919474, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Potassium hydroxide pellets (86%, 4.47 g, 68.5 mmol) was added to a suspension of (RS,RS,RS)-2-tert-butoxycarbonylamino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-3-carboxylic acid ethyl ester (7.44 g, 17.1 mmol) in tetrahydrofuran/water 1:1 (140 mL). After heating 5 h at reflux, the mixture was concentrated in vacuo. The residue was taken up in 1M aq. potassium phosphate buffer (pH 6.85) and dichloromethane, and ethanol was added until a clear two-phase mixture was obtained. The organic layer was separated, washed with brine and evaporated to afford the title compound (6.91 g, 99%). Light yellow solid, MS (ISP) 405.3 (M−H)−.

Workup

  1. temperatureAfter heating 5 h
  2. temperatureat reflux
  3. concentrationthe mixture was concentrated in vacuo
  4. additiondichloromethane, and ethanol was added until a clear two-phase mixture
  5. customwas obtained
  6. customThe organic layer was separated
  7. washwashed with brine
  8. customevaporated

Sources & evidence

ORD record
ord-69f9cd3856c34e398baf97b75bed088e
Source dataset
uspto-grants-2006_10
Patent number
US07122555B2

Reaction notes

Loading…