Sodium hydride → HCID 21838614, compound

HRID 1740471Notes

Reaction equation

HRID 1740471 reaction equation
[C:1]([O:5][C:6]([NH:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH2:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2549512-(2-Chloroethoxy)tetrahydro-2H-pyranHCID 736159Tert-butyl N-(benzyloxy)carbamate

Product 1

HCID 21838614HCID 21838614, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-tert-butyloxycarbonyl-O-benzylhydroxylamine 28 (5.79 g, 25.96 mmol) in dry DMF (50 ml) was added NaH (60%, 1.2 g, 30 mmol) slowly during 15 min period under argon atmosphere at 0° C. The reaction was allowed to stir at 0° C. for 30 min and at room temperature for 1 h. 1-Chloro-2-(tetrahydropyranyl)oxy-ethane 29 (4.95 g, 30 mmol) was added and the reaction mixture was heated at 80° C. for 12 h. The reaction was cooled and evaporated to dryness. The residue was suspended in water (50 ml), pH of the solution adjusted to 7 and extracted in EtOAc (150 ml). The EtOAc extract was washed with water and brine, dried and evaporated to dryness. The residue was purified by flash chromatography over silica gel using hexane→CH2Cl2 as the eluent. The required fractions were collected and evaporated to give 6.0 g (66%) of an oily product. 1HNMR (CDCl3): δ1.48 (s, 9H, Boc), 1.49-1.84 (m, 6H, 3.CH2), 3.48-3.70 (m, 4H, 2.CH2), 3.86 (m, 2H, CH2), 4.60 (t, 1H, CH), 4.84 (s, 2H, CH2Ph) and 7.32-7.42 (m, 5H, Ph).

Workup

  1. temperaturethe reaction mixture was heated at 80° C. for 12 h
  2. temperatureThe reaction was cooled
  3. customevaporated to dryness
  4. extractionextracted in EtOAc (150 ml)
  5. extractionThe EtOAc extract
  6. washwas washed with water and brine
  7. customdried
  8. customevaporated to dryness
  9. customThe residue was purified by flash chromatography over silica gel
  10. customThe required fractions were collected
  11. customevaporated

Sources & evidence

ORD record
ord-86087643f358410eae078b585d0beedc
Source dataset
uspto-grants-1999_10
Patent number
US05969135

Reaction notes

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