Sodium hydride → (S)-tert-Butyl 1-cyclopropyl-3-(2-methoxyethoxy)propan-2-ylcarbamate

HRID 632209Notes

Reaction equation

HRID 632209 reaction equation
[H-].[Na+].[CH:3]1([CH2:6][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:8][OH:9])[CH2:5][CH2:4]1.Br[CH2:19][CH2:20][O:21][CH3:22]>C1COCC1>[CH:3]1([CH2:6][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH2:8][O:9][CH2:19][CH2:20][O:21][CH3:22])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 59227079(S)-tert-Butyl 1-cyclopropyl-3-hydroxypropan-2-ylcarbamate

Product 1

HCID 71105632(S)-tert-Butyl 1-cyclopropyl-3-(2-methoxyethoxy)propan-2-ylcarbamateYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (70%, 0.504 g, 15 mmol) was added in portions to a solution of (S)-tert-butyl 1-cyclopropyl-3-hydroxypropan-2-ylcarbamate (1.6 g, 7.5 mmol) in THF (30 mL) at room temperature. The mixture was stirred at room temperature for 20 min. 1-Bromo-2-methoxyethane (2.07 g, 15 mmol) was added and stirring was continued for 2 h. The reaction was quenched by careful addition of H2O (5 mL). After evaporation of solvent the residue was diluted with ethyl acetate (20 mL) and H2O (20 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4, and concentrated to give the title product as yellow oil (1.01 g, 50%); MS (EI): m/e=296.2 [M+Na]+.

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe reaction was quenched by careful addition of H2O (5 mL)
  4. customAfter evaporation of solvent the residue
  5. additionwas diluted with ethyl acetate (20 mL) and H2O (20 mL)
  6. washThe organic layer was washed with brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-88aed089fff7435683449281357b38a5
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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