Butyl isocyanate → HCID 14988927, compound

HRID 481330Notes

Reaction equation

HRID 481330 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[O:6][C:5]1([CH:8]1[CH:15]([O:16][CH3:17])[CH:14]([O:18][C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])[CH2:13][CH2:12][C:9]21[O:11][CH2:10]2)[CH3:7].[H-].[Na+].[CH2:29]([N:33]=[C:34]=[O:35])[CH2:30][CH2:31][CH3:32]>O1CCCC1.C(OCC)C>[CH2:29]([NH:33][C:34]([O:1][CH2:2][CH2:3][CH:4]1[O:6][C:5]1([CH:8]1[CH:15]([O:16][CH3:17])[CH:14]([O:18][C:19]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[O:20])[CH2:13][CH2:12][C:9]21[O:11][CH2:10]2)[CH3:7])=[O:35])[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 8110Butyl isocyanateHCID 24758Sodium hydrideHCID 14988919HCID 14988919, compound

Product 1

HCID 14988927HCID 14988927, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[3-(2-hydroxyethyl)-2-methyloxiranyl]-5-methoxy-6-(morpholinocarbonyloxy)-1-oxaspiro[2,5]octane (11.1 mg) in anhydrous tetrahydrofuran (1 ml) was added sodium hydride (60% oil dispersion, 2.4 mg) in one portion under ice cooling. The mixture was stirred for half an hour at the same temperature and butyl isocyanate (4.5 mg) was added. After stirred for 2 hours at ambient temperature, the solvent was diluted with diethyl ether (2 ml) and washed with water, dried, and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (ethyl acetate) to afford 4-[3-(2-butylcarbamoyloxyethyl)-2-methyloxiranyl]-5-methoxy-6-(morpholinocarbonyloxy)-1-oxaspiro[2,5]octane (10.8 mg).

Workup

  1. additionwas added
  2. washwashed with water
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-c47ea1eb80df486cba15613b82069b21
Source dataset
uspto-grants-1998_08
Patent number
US05789405

Reaction notes

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