Water → (1,1-Dimethylallyl)carbamic acid tert-butyl ester

HRID 660523Notes

Reaction equation

HRID 660523 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]([O:15][C:16](=[O:23])[NH:17][C:18]([CH3:22])([CH3:21])[CH:19]=O)([CH3:14])([CH3:13])[CH3:12].O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:11]([O:15][C:16](=[O:23])[NH:17][C:18]([CH3:22])([CH3:21])[CH:19]=[CH2:1])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 3251421Potassium bis(trimethylsilyl)amideHCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

Product 1

HCID 13294366(1,1-Dimethylallyl)carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of methyl triphenylphosphonium bromide (1.9 g, 5 mmol) in THF (25 mL) at −78° C. is added dropwise KHMDS (5 mmol, 11 mL of 0.5M solution). The mixture is stirred at 0° C. for 30 min then is recooled to −78° C. To this is added dropwise a solution of (1,1-dimethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (1.0 g, 5 mmol) in THF (5 mL). The mixture is stirred at −78° C. for 10 min then is allowed to warm to RT overnight. Water is added and the mixture is extracted with EtOAc. The organic phase is dried over magnesium sulfate and the solvent removed under reduced pressure. The resulting oil is purified by flash chromatography to give the title compound.

Workup

  1. customthen is recooled to −78° C
  2. stirringThe mixture is stirred at −78° C. for 10 min
  3. temperatureto warm to RT overnight
  4. extractionthe mixture is extracted with EtOAc
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customthe solvent removed under reduced pressure
  7. customThe resulting oil is purified by flash chromatography

Sources & evidence

ORD record
ord-74e6ce0ce0b24a098c3f12b79dcc1662
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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