Hydrochloric Acid → HCID 11544681, compound

HRID 349775Notes

Reaction equation

HRID 349775 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.[CH3:21][N:22]([CH3:32])[C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1.Cl>CN(C)C1C=CN=CC=1.ClCCl>[CH3:21][N:22]([CH3:32])[C:23]1[CH:28]=[CH:27][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:25][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27333724-(Dimethylamino)phenyl isocyanateHCID 58586461(1S)-1,8,8-trimethylbicyclo[3.2.1]octane-2,4-dione

Product 1

HCID 11544681HCID 11544681, compound

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 (25 mL) was added a solution of 4-(dimethylamino)phenyl isocyanate (0.32 g, 2.0 mmole) in dry dichloromethane (5 mL). The resulting reaction mixture was allowed to stir overnight under a nitrogen atmosphere, during which time it came up to room temperature. It was then stirred at 30° C. for seven hours. The resulting mixture was treated with 2N aqueous HCl (30 mL) and the layers were separated. The acidic aqueous layer was extracted with two additional portions of dichloromethane (50 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator. The desired product was isolated by chromatography on silica gel (10% ethyl acetate/hexane) and recrystallized from 95% ethanol to yield the title compound as a light gray solid (0.16 g, 23% yield), mp=93–95° C.; MS (−) ESI m/z=341 (M−H)−; [α]D25=−23.8° (c=1, EtOH).

Workup

  1. customThe resulting reaction mixture
  2. customcame up to room temperature
  3. stirringIt was then stirred at 30° C. for seven hours
  4. customthe layers were separated
  5. extractionThe acidic aqueous layer was extracted with two additional portions of dichloromethane (50 mL)
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-e332dc0945b94d8f87bd8640904e00f1
Source dataset
uspto-grants-2007_02
Patent number
US07179943B2

Reaction notes

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