Benzyl Alcohol → HCID 53685280, compound

HRID 1379500Notes

Reaction equation

HRID 1379500 reaction equation
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:19])([C:7]3[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:20].C(Cl)(=O)C(Cl)=O.[CH2:27](O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.N1C=CC=CC=1>CN(C)C=O.C1COCC1.C(Cl)(Cl)Cl.C1C=CC=CC=1>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:19])([C:7]3[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:17])=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:20]

Participants

9

Reactant 4

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 65578Oxalyl chlorideHCID 22872084HCID 22872084, compound

Product 1

HCID 53685280HCID 53685280, compoundYield 8%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 50 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-carboxy-10b-methyl-1,2,3,4,4a,-5,6,10b-octahydrobenzo[f]quinolin-3-one (100 mg, 0.37) and 2 mL of benzene. Oxalyl chloride (1.1 mmol) was added dropwise via syringe to the stirred mixture, followed by a catalytic amount of dimethylformamide (one drop). The mixture was allowed to stir at room temperature for 25 min, and then the volatiles were removed in vacuo. One mL of THF was added, followed by a solution of benzyl alcohol and pyridine (4 eq) in 1 mL of THF at 0°. It was then allowed to warm to room temperature, diluted with 50 mL of chloroform, and washed with 0.1N hydrochloric acid (2×25 mL), 10% sodium bicarbonate (2×25 mL), water, (2×25 mL), and brine (2×25 mL). The combined organic extracts were dried over sodium sulfate, concentrated and chromatographed on silica (ethyl acetate eluent), to give 11 mg (8%) of the title compound as an amorphous yellow foam. FDMS: m/e=349.

Workup

  1. customthe volatiles were removed in vacuo
  2. additionOne mL of THF was added
  3. temperatureto warm to room temperature
  4. washwashed with 0.1N hydrochloric acid (2×25 mL), 10% sodium bicarbonate (2×25 mL), water, (2×25 mL), and brine (2×25 mL)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated
  7. customchromatographed on silica (ethyl acetate eluent)

Sources & evidence

ORD record
ord-e5e576bdb61445aa82d7ed773095966b
Source dataset
uspto-grants-1997_09
Patent number
US05670514

Reaction notes

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