Sodium hydride → tert-Butyl ((3aS,4R,6S,6aR)-6-(2-(benzyloxy)ethoxy)-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate

HRID 923293Notes

Reaction equation

HRID 923293 reaction equation
[OH:1][C@@H:2]1[C@H:6]2[O:7][C:8]([CH3:11])([CH3:10])[O:9][C@H:5]2[C@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:3]1.[H-].[Na+].CC1C=CC(S(O[CH2:33][CH2:34][O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=O)=O)=CC=1>CN(C=O)C>[CH2:36]([O:35][CH2:34][CH2:33][O:1][C@@H:2]1[C@H:6]2[O:7][C:8]([CH3:10])([CH3:11])[O:9][C@H:5]2[C@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:3]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5613752-(Benzyloxy)ethyl 4-methylbenzenesulfonateHCID 15382963tert-butyl N-[(3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]carbamate

Product 1

HCID 89652923tert-Butyl ((3aS,4R,6S,6aR)-6-(2-(benzyloxy)ethoxy)-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl ((3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d]-[1,3]dioxol-4-yl)carbamate (3.0 g, 10.8 mmol) in dry DMF (30 mL) under nitrogen atmosphere was cooled at 0° C. followed by addition of NaH (60%, 530 mg, 13.0 mmol). After stirring for 30 min at 0° C., 2-(benzyloxy)ethyl 4-methylbenzenesulfonate (3.3 g, 10.8 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 (30 mL). To the mixture was extracted 3×30 mL of n-hexane. The combined organic phases were dried over MgSO4, filtered and evaporated to the dryness. The pure IIIc 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 (30 mL)
  4. extractionTo the mixture was extracted 3×30 mL of n-hexane
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to the dryness
  8. customThe pure IIIc was isolated from reaction mixture by chromatography on silica gel column (mobile phase: n-hexane/EtOAc)

Sources & evidence

ORD record
ord-395fc9f49efd4848986a3689ad1d13e8
Source dataset
uspto-grants-2016_03
Patent number
US09278972B2

Reaction notes

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