Methanol → 1-Adamantyl carbamate

HRID 2092023

Reaction equation

HRID 2092023 reaction equation
[C:1]12([OH:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.ClC(Cl)(Cl)[C:14]([N:16]=C=O)=[O:15].CO.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:14](=[O:15])([O:11][C:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2)[NH2:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 641521-AdamantanolHCID 76400Trichloroacetyl isocyanate

Product 1

HCID 124376461-Adamantyl carbamateYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Adamantanol (1.52 g, 10.0 mmol) in dichloromethane (30 mL) was mixed with trichloroacetyl isocyanate (1.40 mL, 11.8 mmol) at 0° C., then warmed to room temperature and stirred for 2 hours. After completion of the reaction, the reaction solution was evaporated under reduced pressure, and the resulting crude reaction product was mixed with methanol (15 mL) and saturated aqueous potassium carbonate and stirred at 50° C. for 1 day. After completion of the reaction, the methanol was removed by vacuum distillation, and the residue was filtered. The resulting solid was washed with water and dried under reduced pressure to give the desired product (74% yield, 2 steps).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction solution was evaporated under reduced pressure
  3. customthe resulting crude reaction product
  4. stirringstirred at 50° C. for 1 day
  5. customAfter completion of the reaction
  6. customthe methanol was removed by vacuum distillation
  7. filtrationthe residue was filtered
  8. washThe resulting solid was washed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-4d49707e34924196974f4073021abddf
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Linked notes

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