Dichloromethane → 4-Benzyloxy-1-methoxy-isoquinoline-3-carboxylic acid butyl ester

HRID 1406201Notes

Reaction equation

HRID 1406201 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([OH:26])[C:11]2[C:16]([C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:27](Cl)Cl>O>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([O:26][CH3:27])[C:11]2[C:16]([C:17]=1[O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 178450844HCID 178450844, compound

Product 1

HCID 667129544-Benzyloxy-1-methoxy-isoquinoline-3-carboxylic acid butyl esterYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-benzyloxy-1-hydroxy-isoquinoline-3-carboxylic acid butyl ester (1 eq.), Me3OBF4 (6 eq), KHCO3 (14 eq) and CH2Cl2 (10 ml/mmol 4-benzyloxy-1-hydroxy-isoquinoline-3-carboxylic acid butyl ester) was stirred at ambient temperature for 24 h. Then water (10 ml/mmol) was added and the mixture was extracted with CH2Cl2 (40 ml/mmol). The organic phase was separated, dried over MgSO4 and evaporated in vacuo to give a yellowish solid. The crude product was purified by flash column chromatography on silica gel using hexanes:EtOAc=85:15 as the eluent. Evaporation of the first fraction gave the title compound as a colorless oil in 20% yield; 1H NMR (CDCl3): δ=8.21 to 8.25 (m, 1 H), 8.05 to 8.09 (m, 1 H), 7.33 to 7.73 (m, 7 H), 5.13 (s, 2 H), 4.38 (t, 2 H), 4.16 (s, 3 H), 1.69 (m, 2 H), 1.37 (m, 2 H), 0.94 (t, 3 H).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (40 ml/mmol)
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customto give a yellowish solid
  6. customThe crude product was purified by flash column chromatography on silica gel
  7. customEvaporation of the first fraction

Sources & evidence

ORD record
ord-30309588d58c4f8fa2ff7fbd181db11a
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

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