tert-Butanol → tert-Butyl oxolan-3-ylcarbamate

HRID 556660Notes

Reaction equation

HRID 556660 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3](C(O)=O)[CH2:2]1.C([N:11]([CH2:14]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:23])C=CC=CC=1.[C:33]([OH:37])([CH3:36])([CH3:35])[CH3:34]>CN(C=O)C.CCOC(C)=O>[C:33]([O:37][C:14](=[O:23])[NH:11][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)([CH3:36])([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 4661317(R)-Tetrahydro-3-furoic acid

Product 1

HCID 45091846tert-Butyl oxolan-3-ylcarbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under Ar, to a soln of (+/−)-tetrahydro-3-furoic acid (500 mg, 4.30 mmol) in DMF (2 mL) was added triethylamine(0.66 mL, 4.74 mmol), followed by diphenylphosphoryl azide (1.02 mL, 4.74 mmol). The mixture was heated to 80° for 3 h and cooled to 23°, tert-butanol (3 mL) was then added and the resulting mixture was stirred at 23° for 16 h. The mixture was diluted with EtOAc and washed with H2O. The organic layer was dried over Na2SO4, and concentrated to give the crude intermediate 670 mg.

Workup

  1. temperatureThe mixture was heated to 80° for 3 h
  2. temperaturecooled to 23°
  3. washwashed with H2O
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1cba1a4dd03841929efcf521d0ad3e2a
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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