Water → HCID 15117327, compound

HRID 1029676Notes

Reaction equation

HRID 1029676 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]([CH:21](OS(C)(=O)=O)[CH3:22])[CH:12]([O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C(OCC)(=O)C.O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH:12]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[CH3:13])[CH:21]1[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 15117326HCID 15117326, compound

Product 1

HCID 15117327HCID 15117327, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
38 °C

Procedure

To a solution of N-t-butyloxycarbonyl-N-{3-(1-methanesulfonyloxyethyl)-4-(tetrahydropyran-2-yloxy)pentyl}amine (17 g) in dimethylformamide (200 ml) was added sodium hydride (6.6 g in 60% oil) at 0° C. After stirring for 4 hours at 38° C., the solution was poured into a mixture of ethyl acetate (400 ml) and water (400 ml). The organic layer was washed with water, 1N-hydrochloride solution, saturated sodium bicarbonate, and brine successively. The dried solution was evaporated and then the residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (3:1, V/V) to give 1-t-butyloxycarbonyl-2-methyl-3-(1-tetrahydropyranyloxyethyl)pyrrolidine (10.5 g).

Workup

  1. washThe organic layer was washed with water, 1N-hydrochloride solution, saturated sodium bicarbonate, and brine successively
  2. customThe dried solution was evaporated
  3. customthe residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (3:1, V/V)

Sources & evidence

ORD record
ord-02d753b775f4444fa8b44e00b73fc253
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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