Triethylamine → HCID 59226759, compound

HRID 2407366Notes

Reaction equation

HRID 2407366 reaction equation
C([O-])=O.[NH4+].[OH:5][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([C:9]3=O)[CH2:7]1)[CH2:13]2.C([N:19](CC)CC)C.[CH3:24][C:25]([O:28][C:29]([O:31]C(OC(C)(C)C)=O)=O)([CH3:27])[CH3:26]>CO.[Pd]>[C:25]([O:28][C:29](=[O:31])[NH:19][CH:9]1[CH:8]2[CH2:14][CH:12]3[CH2:13][C:6]([OH:5])([CH2:15][CH:10]1[CH2:11]3)[CH2:7]2)([CH3:27])([CH3:26])[CH3:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 64184IdramantoneHCID 90495Di-tert-butyl dicarbonateHCID 2723923Ammonium formate

Product 1

HCID 59226759HCID 59226759, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Ammonium formate (10 g, 0.15 mol) was added to a solution of 5-hydroxyadamantan-2-one (4.5 g, 0.027 mol, prepared as described in Tetrahedron 1968, 24, 5369) in MeOH (50 ml). Then 10% Pd—C (500 mg) was added carefully and the solution heated under reflux for 1 h. It was then filtered through celite and to this filtrate at 0° C. was added triethylamine (11.2 ml, 0.081 mol) and Boc anhydride (7.06 g, 0.0324 mol). The solution was stirred for 4 h at 20° C. and then concentrated under reduced pressure. The residue was diluted with water and extracted with EtOAc. The organic layer was dried and concentrated to give (5-hydroxyadamantan-2-yl)carbamic acid tert-butyl ester (7 g, 96%). LC-MS (m/z): 168 (M+1). 1H NMR (300 MHz, DMSO-d6): δ 6.8 (d, 1H), 6.7 (brs, 1H), 3.45 (d, 1H), 2.0 (s, 1H), 1.75-1.95 (m, 4H), 1.5-1.7 (m, 6H), 1.35 (s, 9H), 1.25 (t, 2H).

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 1 h
  3. filtrationIt was then filtered through celite and to this filtrate at 0° C.
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was diluted with water
  6. extractionextracted with EtOAc
  7. customThe organic layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-61c4d0e2fa1e4832a31374bd17885730
Source dataset
uspto-grants-2014_08
Patent number
US08809540B2

Reaction notes

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