Water → HCID 86744697, compound
Reaction equation
[OH:1][CH:2](/[CH:12]=[CH:13]/[C:14]1[N:15]([CH3:31])[C:16](=[O:30])[C:17]2[C:22]([C:23]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:3][C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[BH4-].[Na+].O>CO>[OH:11][CH:4]([CH2:3][CH:2]([OH:1])/[CH:12]=[CH:13]/[C:14]1[N:15]([CH3:31])[C:16](=[O:30])[C:17]2[C:22]([C:23]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of ethyl (E)-5-hydroxy-7-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)-3-oxohept-6-enoate (0.35 g; prepared as described hereinafter in Reference Example 1) in methanol (15 ml) at 0° C. was treated with sodium borohydride (0.02 g). The mixture was stirred for one hour and then a further portion of sodium borohydride (0.05 g) was added and stirring was continued for another period of 30 minutes. The resulting clear yellow solution was poured into water (100 ml), forming a white solid. The mixture was extracted with diethyl ether (3×75 ml) and the combined extracts were dried over magnesium sulphate and evaporated, to give ethyl (E)-3,5-dihydroxy-7-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)hept-6-enoate (0.35 g) in the form of a yellow solid.
Workup
- stirringstirring
- waitwas continued for another period of 30 minutes
- customforming a white solid
- extractionThe mixture was extracted with diethyl ether (3×75 ml)
- dry with materialthe combined extracts were dried over magnesium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-5b0fe90dc0ee4e9f8d8f375066f25e2d
- Source dataset
- uspto-grants-1991_04
- Patent number
- US05004747
Reaction notes
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