Benzyl succinimido carbonate → Benzyl (3-hydroxy-2,2-dimethylpropyl)carbamate

HRID 1695021Notes

Reaction equation

HRID 1695021 reaction equation
[CH2:1]([O:8][C:9]([O:11]N1C(=O)CCC1=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][OH:23]>O1CCCC1>[CH2:1]([O:8][C:9]([NH:19][CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][OH:23])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 1173261-Propanol, 3-amino-2,2-dimethyl-

Product 1

HCID 23078902Benzyl (3-hydroxy-2,2-dimethylpropyl)carbamateYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

50.0 g of N-(benzyloxycarbonyloxy)succinimide (200 mmol) was added to a solution of 13.8 g of 3-amino-2,2-dimethylpropanol (134 mmol) in tetrahydrofuran (140 ml), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure and diluted with water, followed by extraction with ethyl acetate. Then, the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene/ethyl acetate=9/1-3/1) to obtain 29.52 g of the title compound (yield: 93%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent: toluene/ethyl acetate=9/1-3/1)

Sources & evidence

ORD record
ord-8506c4b74ee74188b6960bf8675d9e6e
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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