Pyridine → HCID 22877093, compound

HRID 1379554Notes

Reaction equation

HRID 1379554 reaction equation
[CH3:1][N:2]1[C@H:11]2[C@@:6](C)([C:7]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:24].N1C=CC=C[CH:26]=1.ClCCl.[C:34](Cl)(=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36]>C(Cl)(Cl)Cl>[CH3:1][N:2]1[C@H:11]2[C@@H:6]([C:7]3[C:15]([CH3:26])=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[CH:17]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:24]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 62493Pivaloyl chlorideHCID 54238570HCID 54238570, compound

Product 1

HCID 22877093HCID 22877093, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-(3-aminophenyl)-10b-methyl 1,2,3,4,4a,-5,6,10b octahydrobenzo[f]quinolin-3-one (31 mg, 0.097 mmol), N,N-dimethylaminopyridine (3 mg, 0.024 mmol), 1 mL of pyridine and 0.5 mL of dichloromethane. The solution was cooled to 0°, and excess pivaloyl chloride (0.086 mL, 0.69 mmol) was added. The stirred mixture was allowed to warm to room temperature over 2 h. The mixture was diluted with chloroform, and washed with 5% aqueous hydrochloric acid solution, water, 5% aqueous sodium hydroxide solution, water, and the combined organic extracts were dried over sodium sulfate, concentrated and chromatographed on silica gel (ethyl acetate eluent) to give 25 mg (64%) of the title compound as a yellow solid. mp 95°-98°. FDMS m/e=404. α[D]589 =+62.50 (c=0.16, chloroform).

Workup

  1. temperatureThe solution was cooled to 0°
  2. washwashed with 5% aqueous hydrochloric acid solution, water, 5% aqueous sodium hydroxide solution, water
  3. dry with materialthe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customchromatographed on silica gel (ethyl acetate eluent)

Sources & evidence

ORD record
ord-61111cf1c4ac443aa1b0a5c59c98c347
Source dataset
uspto-grants-1997_09
Patent number
US05670514

Reaction notes

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