Ethanol → HCID 9905714, compound

HRID 1830950Notes

Reaction equation

HRID 1830950 reaction equation
[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+].[CH3:9][O:10][C:11]1[C:12]([O:41][CH3:42])=[CH:13][C:14]2[N:20](COCC[Si](C)(C)C)[C:19](=O)[C@@H:18]3[CH2:30][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:32][N:17]3[C:16](=[O:39])[C:15]=2[CH:40]=1.CCO.C1COCC1>C(OCC)(=O)C.C(Cl)(Cl)Cl.CO>[CH3:9][O:10][C:11]1[C:12]([O:41][CH3:42])=[CH:13][C:14]2[N:20]=[CH:19][C@@H:18]3[CH2:30][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:32][N:17]3[C:16](=[O:39])[C:15]=2[CH:40]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 69621552HCID 69621552, compoundHCID 131720822Sodium tetraborohydride

Product 1

HCID 9905714HCID 9905714, compoundYield 101.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid sodium tetraborohydride (287 mg, 7.6 mmol, 10 equiv.) was added in one portion to a rapidly stirred solution of 180 (365 mg, 0.76 mmol) in a mixture of anhydrous EtOH (8 mL) and anhydrous THF (8 mL) at 0° C. The reaction mixture was allowed to stir at room temperature for 1 hour at room temperature at which time TLC (5% methanol; 95% chloroform) revealed the complete consumption of starting material. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water (2×100 mL), brine (100 mL) and dried over magnesium sulphate. Filtration and evaporation of excess solvent afforded the crude product as a brown viscous oil. Flash chromatography (silica gel, 70% 40-60° petroleum ether, 30% ethyl acetate yield the final product (181) (271 mg, 0.77 mmol, 74%). 1H NMR (270 MHz, CDCl3) δ7.89 (d, 1H, J=4.03 Hz), 7.53 (s, 1H), 7.51 (s, 1H), 7.40-7.20 (m, 5H), 6.83 (s, 1H), 4.50-4.35 (m, 1H), 3.96 (s, 3H), 3.94 (s, 3H), 3.66-3.36 (m, 2H). 13C NMR (67.8 MHz, CDCl3) δ162.6, 161.5, 151.9, 147.8, 140.4, 133.3, 128.8, 127.6, 127.1, 124.9, 123.6, 119.0, 111.6, 109.8, 56.2, 53.9, 35.4. HRMS (FAB) calcd for C20H19N2O3 (M+.+1) 335.1398, found 335.1396.

Workup

  1. customthe complete consumption of starting material
  2. additionThe reaction mixture was diluted with ethyl acetate (100 mL)
  3. washwashed with water (2×100 mL), brine (100 mL)
  4. dry with materialdried over magnesium sulphate
  5. filtrationFiltration and evaporation of excess solvent
  6. customafforded the crude product as a brown viscous oil

Sources & evidence

ORD record
ord-df5defbfeeed40f8a0a2a7c7d8ba1a2f
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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