tert-Butanol → Tert-butyl [4-(adamantan-1-yl)phenyl]carbamate

HRID 1626770Notes

Reaction equation

HRID 1626770 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([N:20]([CH2:23][CH3:24])[CH2:21]C)C.[C:25]([OH:29])([CH3:28])([CH3:27])[CH3:26].[C:30]12([C:40]3[CH:48]=CC(C(O)=O)=[CH:42][CH:41]=3)[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2>C1COCC1>[C:30]12([C:40]3[CH:48]=[CH:24][C:23]([NH:20][C:21](=[O:8])[O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:42][CH:41]=3)[CH2:37][CH:36]3[CH2:35][CH:34]([CH2:33][CH:32]([CH2:38]3)[CH2:31]1)[CH2:39]2

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 37368544-(1-adamantyl)benzoic Acid

Product 1

HCID 86661495Tert-butyl [4-(adamantan-1-yl)phenyl]carbamateYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

1.18 g (4.29 mmol) of diphenylphosphoryl azide and 434 mg (4.29 mmol) of triethylamine were added to 30 mL of a tert-butanol suspension comprising 1.0 g (3.9 mmol) of 4-(adamantan-1-yl)benzoic acid at 0° C. The mixture was stirred at 80° C. for 4.5 hours, and 40 mL of THF was added. The mixture was stirred for an additional 2 hours. Thereafter, the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue, and the resultant was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline in this order. The resultant was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, thereby giving 679 mg of tert-butyl [4-(adamantan-1-yl)phenyl]carbamate (yield: 53%).

Workup

  1. stirringThe mixture was stirred for an additional 2 hours
  2. distillationThereafter, the solvent was distilled off under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. washthe resultant was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline in this order
  5. dry with materialThe resultant was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained crude product
  8. customwas separated
  9. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-7f3994c1cac346ad86b02872916c4b00
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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