HCID 118177257, compound → 1,1-Dimethylethyl N-[1-(2-hydroxyethyl)cyclopropyl]carbamate

HRID 1485046Notes

Reaction equation

HRID 1485046 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:13][CH2:12]1)C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[C:17]([O:16][C:15](=[O:21])[NH:14][C:11]1([CH2:10][CH2:9][OH:8])[CH2:12][CH2:13]1)([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 118177257HCID 118177257, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 129931391,1-Dimethylethyl N-[1-(2-hydroxyethyl)cyclopropyl]carbamateYield 98.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution in ethanol (112 mL) of the compound (16.3 g) obtained in step (3) above, 20% palladium hydroxide/carbon (3.25 g) was added and the mixture was stirred at 60° C. for 23 hours in a hydrogen atmosphere. After being cooled to room temperature, the reaction mixture was filtered through Celite (registered trademark). The filtrate was concentrated under reduced pressure to give tert-butyl[1-(2-hydroxyethyl)cyclopropyl]carbamate as a colorless solid (11.1 g).

Workup

  1. filtrationthe reaction mixture was filtered through Celite (registered trademark)
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c63cc99bd0b3417d8b227f29b052ac8e
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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