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

HRID 923294Notes

Reaction equation

HRID 923294 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][C:36]([CH3:39])([CH3:38])[CH3:37])(=O)=O)=CC=1>CN(C=O)C>[C: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)([CH3:39])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 146138032-(Tert-butoxy)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 89652920tert-Butyl ((3aS,4R,6S,6aR)-6-(2-(tert-butoxy)ethoxy)-2,2-dimethyltetrahydro-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 (7.0 g, 25.6 mmol) in dry DMF (70 mL) under nitrogen atmosphere was cooled at 0° C. followed by addition of NaH (60%, 1.3 g, 30.7 mmol). After stirring for 30 min at 0° C., 2-(tert-butoxy)ethyl 4-methylbenzenesulfonate (7.0 g, 25.6 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 (70 mL). To the mixture was extracted 3×100 mL of n-hexane. The combined organic phases were dried over MgSO4, filtered and evaporated to the dryness. The pure IIId 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 (70 mL)
  4. extractionTo the mixture was extracted 3×100 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 IIId was isolated from reaction mixture by chromatography on silica gel column (mobile phase: n-hexane/EtOAc)

Sources & evidence

ORD record
ord-e9a30faa4ca943788727cbcd71e80a65
Source dataset
uspto-grants-2016_03
Patent number
US09278972B2

Reaction notes

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