Methylamine → HCID 86700718, compound

HRID 572481Notes

Reaction equation

HRID 572481 reaction equation
[CH3:1][C:2]([Si:5]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[O:6][CH2:7][C@H:8]([C:10]1[O:11][C:12](=O)[C:13]2[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=2[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[CH:17]=1)[OH:9])([CH3:4])[CH3:3].C1COCC1.[CH3:46][NH2:47]>>[Si:5]([O:6][CH2:7][C@H:8]([C:10]1[N:47]([CH3:46])[C:12](=[O:11])[C:13]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[CH:17]=1)=[CH:24][CH:25]=[CH:26][CH:27]=2)[OH:9])([C:2]([CH3:3])([CH3:1])[CH3:4])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 86700717(R)-3-(2-((tert-butyldiphenylsilyl)oxy)-1-hydroxyethyl)-4-(3,4-dimethylphenyl)-1H-isochromen-1-one

Product 1

HCID 86700718HCID 86700718, compoundYield 14%

Conditions

Temperature
80 °C

Procedure

A solution of 3-((1R)-2-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}-1-hydroxyethyl)-4-(3,4-dimethylphenyl)-1H-2-benzopyran-1-one (92 mg, 0.168 mmol) was dissolved in 2M methyl amine in THF (1.3 mL, 2.51 mmol) was heated to 80° C. After 18 h, the reaction mixture was concentrated in vacuo and treated with 4M HCl in dixoane (2 mL). The reaction stirred for 20 min and poured into 1M aqueous NaOH and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-50%) to afford the title compound (13 mg, 0.023 mmol, 14% yield) as a colorless film: Rt=1.28, ES+ MS: 562 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiontreated with 4M HCl in dixoane (2 mL)
  3. additionpoured into 1M aqueous NaOH
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-50%)

Sources & evidence

ORD record
ord-bc02894292ff43c0ab07aa25ad51baa9
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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