tert-butyl N-methyl-N-(3-oxopropyl)carbamate → HCID 85790426, compound

HRID 1243604Notes

Reaction equation

HRID 1243604 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][CH:12]=[O:13])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[CH2:14]([Mg]Cl)[CH2:15][CH3:16]>O1CCCC1.CCOCC>[OH:13][CH:12]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 10442454tert-butyl N-methyl-N-(3-oxopropyl)carbamateHCID 178455855HCID 178455855, compound

Product 1

HCID 85790426HCID 85790426, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled stirred solution of methyl-(3-oxopropyl)carbamic acid, 1,1-dimethylethyl ester (11.0 g, 59 mmol) in dry tetrahydrofuran (120 ml) under nitrogen was added a 2M solution of n-propylmagnesium chloride in ether (36 ml). The resulting mixture was stirred at 0° C. for 30 minutes, then allowed to warm to room temperature with sting over 20 h, and quenched by dropwise addition of saturated aqueous ammonium chloride. The supernatant solution was decanted from the white solids and concentrated to dryness to give the title compound (11.5 g) as an oil.

Workup

  1. temperatureto warm to room temperature
  2. waitwith sting over 20 h
  3. customquenched by dropwise addition of saturated aqueous ammonium chloride
  4. customThe supernatant solution was decanted from the white solids
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2e220d6e8d2e4086adc4637b0ca5dcf8
Source dataset
uspto-grants-2006_10
Patent number
US07119109B2

Reaction notes

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