Acetic Acid → 3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-4-(morpholinomethyl)-1H-isochromen-1-one

HRID 634380Notes

Reaction equation

HRID 634380 reaction equation
[Si:1]([O:8][CH:9]([C:11]1[O:12][C:13](=[O:23])[C:14]2[C:19]([C:20]=1[CH:21]=O)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl.[O-]S([O-])(=O)=O.[Na+].[Na+]>[Si:1]([O:8][CH:9]([C:11]1[O:12][C:13](=[O:23])[C:14]2[C:19]([C:20]=1[CH2:21][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 1239374753-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1-oxo-1H-isochromene-4-carbaldehyde

Product 1

HCID 1238137353-(1-((tert-butyldimethylsilyl)oxy)ethyl)-4-(morpholinomethyl)-1H-isochromen-1-oneYield 33.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24436Sodium SulfateSolvent

Procedure

To a solution of 3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1-oxo-1H-isochromene-4-carbaldehyde (Intermediate B59.2, 0.5 g, 1.5 mmol) and morpholine (0.12 ml, 1.35 mmol) in DCM (20 ml), dry Na2SO4 was added and the mixture stirred RT for 10 min. Sodium triacetoxyborohydride (0.286 g, 2.25 mmol) and acetic acid (0.09 ml, 1.5 mmol) were added and the reaction mixture was stirred for 24 h at RT. The reaction was quenched by the addition of 2M HCl (3 ml), the heterogeneous mixture was filtered and the filtrate was purified by flash chromatography on silica NH cartridge (cyclohexane:EtOAc=90:10 to 80:20) affording 3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-4-(morpholinomethyl)-1H-isochromen-1-one (Intermediate B59.3, 0.183 g, 0.45 mmol, 30%).

Workup

  1. stirringthe reaction mixture was stirred for 24 h at RT
  2. customThe reaction was quenched by the addition of 2M HCl (3 ml)
  3. filtrationthe heterogeneous mixture was filtered
  4. customthe filtrate was purified by flash chromatography on silica NH cartridge (cyclohexane:EtOAc=90:10 to 80:20)

Sources & evidence

ORD record
ord-b90821fdb1574b92901cce97ff264e98
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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