tert-Butanol → tert-butyl N-(3-methylidenecyclobutyl)carbamate

HRID 577738Notes

Reaction equation

HRID 577738 reaction equation
C=[C:2]1[CH2:5][CH:4]([C:6](O)=O)[CH2:3]1.CC[N:11]([CH2:14]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:23])=CC=1.[C:33]([OH:37])([CH3:36])([CH3:35])[CH3:34]>>[CH2:6]=[C:4]1[CH2:3][CH:2]([NH:11][C:14](=[O:23])[O:37][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:5]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 274753-Methylenecyclobutanecarboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 28875369tert-butyl N-(3-methylidenecyclobutyl)carbamateYield 77%

Procedure

To a solution of 3-methylidenecyclobutanecarboxylic acid (132 g, 1.17 mol) and Et3N (178 g, 1.76 mol) in tert-butyl alcohol (1 L) was added dropwise DPPA (574 g, 1.41 mol) and the resulting mixture was refluxed overnight. The mixture was then quenched with water (100 mL). After removal of the tert-butyl alcohol, the residue was treated with sat. NH4Cl (500 mL), and the resulting solid precipitate was collected, washed with sat. NH4Cl and sat. NaHCO3 to give the title compound (165 g, 77% yield) as a white solid.

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. customThe mixture was then quenched with water (100 mL)
  3. customAfter removal of the tert-butyl alcohol
  4. additionthe residue was treated with sat. NH4Cl (500 mL)
  5. customthe resulting solid precipitate was collected
  6. washwashed with sat. NH4Cl and sat. NaHCO3

Sources & evidence

ORD record
ord-77231d51496e4bd18bf231fabfe39dda
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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