Sodium hydride → (3aS,4R,6S,6aR)-6-(2-(benzyloxy)ethoxy)-2,2-dimethyl-N-trityltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine

HRID 923295Notes

Reaction equation

HRID 923295 reaction equation
[CH3:1][C:2]1([CH3:31])[O:6][C@H:5]2[C@H:7]([NH:11][C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][C@H:9]([OH:10])[C@H:4]2[O:3]1.[H-].[Na+].CC1C=CC(S(O[CH2:45][CH2:46][O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)(=O)=O)=CC=1>CN(C=O)C>[CH2:48]([O:47][CH2:46][CH2:45][O:10][C@@H:9]1[C@H:4]2[O:3][C:2]([CH3:31])([CH3:1])[O:6][C@H:5]2[C@H:7]([NH:11][C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:8]1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5613752-(Benzyloxy)ethyl 4-methylbenzenesulfonateHCID 89644196(3aR,4S,6R,6aS)-2,2-dimethyl-6-(tritylamino)tetrahydro-3aH-cyclopenta[d]-[1,3]dioxol-4-ol

Product 1

HCID 89644011(3aS,4R,6S,6aR)-6-(2-(benzyloxy)ethoxy)-2,2-dimethyl-N-trityltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (10 g, 24.0 mmol) (3aR,4S,6R,6aS)-2,2-dimethyl-6-(tritylamino)tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol in dry DMF (100 mL) under nitrogen atmosphere was cooled at 0° C. followed by addition of NaH (60%, 1.2 g, 29.0 mmol). After stirring for 30 min at 0° C., 2-(benzyloxy)ethyl 4-methylbenzenesulfonate (7.4 g, 24.0 mmol) was added and the reaction mixture was allowed to warm at room temperature. After stirring for 4 hours, the reaction mixture was quenched with water (100 mL). To the mixture was extracted 3×100 mL of EtOAc. The combined organic phases were dried over MgSO4, filtered and evaporated to the dryness. The pure IIIe was isolated from reaction mixture by chromatography on silica gel column (mobile phase: n-hexane/EtOAc).

Workup

  1. temperatureto warm at room temperature
  2. stirringAfter stirring for 4 hours
  3. customthe reaction mixture was quenched with water (100 mL)
  4. extractionTo the mixture was extracted 3×100 mL of EtOAc
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to the dryness
  8. customThe pure IIIe was isolated from reaction mixture by chromatography on silica gel column (mobile phase: n-hexane/EtOAc)

Sources & evidence

ORD record
ord-f1af2320952c4d63ade4295ca16a9164
Source dataset
uspto-grants-2016_03
Patent number
US09278972B2

Reaction notes

Loading…