Lithium Hydroxide → HCID 21840857, compound

HRID 1645815Notes

Reaction equation

HRID 1645815 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=1)=[N:8][CH:7]([CH2:25][O:26]C(=O)C1C=C(OC)C=C(OC)C=1)[CH2:6]2.[OH-].[Li+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=1)=[N:8][CH:7]([CH2:25][OH:26])[CH2:6]2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 19802635HCID 19802635, compound

Product 1

HCID 21840857HCID 21840857, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 98.4 g of [3S] 3,4-dihydro-6,7-dimethoxy-3-[(3,5-dimethoxybenzoyloxy)methyl]-1-(3,5-dimethoxyphenyl)-isoquinoline [Formula IIa: all of R1 to R4 =methoxy], 51 CH3OH and 207 ml aqueous lithium hydroxide, is stirred for 12 hrs. at room temperature. The obtained solution is concentrated under reduced pressure, treated with ethyl acetate and washed with H2O/Na2CO3. The organic phase is dried over K2CO3 and the solvent removed under reduced pressure. The residue is taken up in ethyl ether, crystallized, filtered and dried to yield the title compound: m.p.=59°-62° C., αD20 =-55.19° (c=0.5 in CH3OH).

Workup

  1. customat room temperature
  2. concentrationThe obtained solution is concentrated under reduced pressure
  3. additiontreated with ethyl acetate
  4. washwashed with H2O/Na2CO3
  5. dry with materialThe organic phase is dried over K2CO3
  6. customthe solvent removed under reduced pressure
  7. customcrystallized
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-7a59ed7fde4848e6abf28199293c89e2
Source dataset
uspto-grants-1993_01
Patent number
US05177085

Reaction notes

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