Triethylamine → HCID 11595775, compound

HRID 349774Notes

Reaction equation

HRID 349774 reaction equation
[CH3:1][C@@:2]12[C:9]([CH3:11])([CH3:10])[CH:6]([CH2:7][CH2:8]1)[C:5](=[O:12])[CH2:4][C:3]2=[O:13].C(N(CC)CC)C.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1>CN(C)C1C=CN=CC=1.ClCCl>[F:21][C:22]([F:32])([F:33])[C:23]1[CH:24]=[CH:25][C:26]([NH:29][C:30]([CH:4]2[C:5](=[O:12])[CH:6]3[C:9]([CH3:10])([CH3:11])[C@:2]([CH3:1])([CH2:8][CH2:7]3)[C:3]2=[O:13])=[O:31])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 58586461(1S)-1,8,8-trimethylbicyclo[3.2.1]octane-2,4-dione

Product 1

HCID 11595775HCID 11595775, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of (1S)-1,8,8-trimethylbicyclo[3.2.1]octane-2,4-dione (0.36 g, 2.0 mmole), triethylamine (0.20 g, 2.0 mmole) and 4-(dimethylamino)pyridine (0.24 g, 2.0 mmole) in dry dichloromethane (20 mL) was added a solution of 4-(trifluoromethyl)phenyl isocyanate (0.41 g, 2.2 mmole) in dry dichloromethane (3 mL). The resulting reaction mixture was allowed to stir overnight under a nitrogen atmosphere, during which time it came up to room temperature. The resulting mixture was concentrated on a rotary evaporator and then partitioned between dichloromethane and 2N aqueous HCl. The acidic aqueous layer was extracted with two additional portions of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator to give a yellow oil, which was purified by chromatography on silica gel (10% ethyl acetate/hexane) to yield the title compound as an orange solid (0.36 g, 49% yield), mp=81–83° C.; MS (−) ESI m/z=366 (M−H)−; [α]D25=−25.6° (c=1, EtOH).

Workup

  1. customThe resulting reaction mixture
  2. customcame up to room temperature
  3. concentrationThe resulting mixture was concentrated on a rotary evaporator
  4. custompartitioned between dichloromethane and 2N aqueous HCl
  5. extractionThe acidic aqueous layer was extracted with two additional portions of dichloromethane
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated on a rotary evaporator
  8. customto give a yellow oil, which
  9. customwas purified by chromatography on silica gel (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ef41b822127041ac825b25c07df92b3a
Source dataset
uspto-grants-2007_02
Patent number
US07179943B2

Reaction notes

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