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

HRID 923296Notes

Reaction equation

HRID 923296 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][C:48]([CH3:51])([CH3:50])[CH3:49])(=O)=O)=CC=1>CN(C=O)C>[C: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)([CH3:51])([CH3:50])[CH3:49]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 146138032-(Tert-butoxy)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 89643931(3aS,4R,6S,6aR)-6-(2-(tert-butoxy)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 (3aR,4S,6R,6aS)-2,2-dimethyl-6-(tritylamino)tetrahydro-3aH-cyclopenta[d]-[1,3]dioxol-4-ol (10.0 g, 24.0 mmol) 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-(tert-butoxy)ethyl 4-methylbenzenesulfonate (6.5 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 IIIf 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 IIIf was isolated from reaction mixture by chromatography on silica gel column (mobile phase: n-hexane/EtOAc)

Sources & evidence

ORD record
ord-9925fd212497428686f081c1c8400c67
Source dataset
uspto-grants-2016_03
Patent number
US09278972B2

Reaction notes

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