Ethyl diazoacetate → HCID 57516788, compound

HRID 1917583Notes

Reaction equation

HRID 1917583 reaction equation
[CH2:1]([N:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:9][C:10]([CH3:13])([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N-]>ClC(Cl)C.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][O:12][C:10]([CH3:13])([CH3:11])[CH2:9][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:28]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 13149222HCID 13149222, compound

Product 1

HCID 57516788HCID 57516788, compoundYield 15.9%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

(4.9 g, 18.2 mmol) 1-(Dibenzylamino)-2-methylpropan-2-ol (CAS 344868-41-3) was dissolved in dichloroethane (50 ml) and ethyl 2-diazoacetate (2.83 ml, 27.3 mmol, 1.5 equiv.) and rhodium(II) acetate dimer (200 mg, 0.455 mmol, 0.025 equiv.) were added carefully at room temperature. The mixture was stirred for 3 hours at 80° C. The reaction mixture was evaporated with isolute and the crude product was purified by flash chromatography by directly loading the residue onto a silica gel column and eluting with a heptane:ethyl acetate gradient 100:0 to 70:30. The desired (2-dibenzylamino-1,1-dimethyl-ethoxy)-acetic acid ethyl ester (1.03 g, 80% purity, 13% yield) was obtained as a colorless liquid, MS: m/e=356.3 (M+H+).

Workup

  1. customThe reaction mixture was evaporated with isolute
  2. customthe crude product was purified by flash chromatography
  3. washeluting with a heptane

Sources & evidence

ORD record
ord-edd50a22c37c440cb5dd675128c0c884
Source dataset
uspto-grants-2013_12
Patent number
US08618296B2

Reaction notes

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