Acetaldehyde → HCID 59540229, compound

HRID 923424Notes

Reaction equation

HRID 923424 reaction equation
Cl.[NH2:2][C@H:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH:17](=O)[CH3:18]>CO.[Pd]>[CH2:17]([NH:2][C@H:3]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH3:18]

Participants

5

Reactant 2

HCID 177AcetaldehydeHCID 56777188H-D-Phg-otbu hcl

Product 1

HCID 59540229HCID 59540229, compoundYield 110.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)-tert-butyl 2-amino-2-phenylacetate hydrochloride (0.25 g, 1.026 mmol) in MeOH (10.26 mL) was added 10% Pd/C (0.080 g, 1.026 mmol). The resulting mixture was cooled to 0° C., and acetaldehyde (0.576 mL, 10.26 mmol) was added. The resulting mixture was stirred at 0° C. for 10-15 mins, the ice bath was removed, and the mixture was placed under a hydrogen balloon and stirred at rt for 45 mins. The mixture was filtered through celite, washed with methanol, and the filtrate was concentrated in vacuo to give the title compound (0.267 g).

Workup

  1. customthe ice bath was removed
  2. stirringstirred at rt for 45 mins
  3. filtrationThe mixture was filtered through celite
  4. washwashed with methanol
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e886216a573d4af4bb628dcfe42b508e
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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