Benzaldehyde → HCID 54312559, compound

HRID 1079250Notes

Reaction equation

HRID 1079250 reaction equation
[CH3:1][C@@:2]12[C:11]3[CH:12]=[CH:13][C:14](Br)=[CH:15][C:10]=3[CH2:9][CH2:8][C@H:7]1[NH:6][C:5](=[O:17])[CH2:4][CH2:3]2.C[Li].[CH2:20](OCC)C.C([Li])(C)(C)C.CCCCC.[CH:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1COCC1>[C:35]([C:14]1[CH:13]=[CH:12][C:11]2[C@:2]3([CH3:1])[C@@H:7]([CH2:8][CH2:9][C:10]=2[CH:15]=1)[N:6]([CH3:20])[C:5](=[O:17])[CH2:4][CH2:3]3)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

8

Reactant 6

HCID 240BenzaldehydeHCID 3283Diethyl EtherHCID 8003PentaneHCID 11119935HCID 11119935, compoundHCID 178418306HCID 178418306, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 54312559HCID 54312559, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4aR)-(10bR)-10b-methyl-8-bromo-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one in 25 mL of THF at -78° under an atmosphere of nitrogen was added 330 μL of a 1.4M solution of methyllithium in diethyl ether (0.46 mmol). The reaction mixture turned bright yellow, and after 10 min, 470 μl of a 1.7M solution of t-butyllithium in pentane (0.80 mmol) was added. The reaction mixture was stirred for 10 min before the addition of benzaldehyde (80 μL, 0.79 mmol) as a single aliquot. The reaction was warmed to room temperature and stirred for 30 min before partitioning between diethyl ether and 1N hydrochloric acid. The ether layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to afford 0.1818 g crude product. The material was purified on a Chromatotron (2 mm plate, dry loaded with chloroform, eluted with 5% methanol/chloroform) to give 106 mg of desired product. A portion of this material was triturated with diethyl ether to yield a white solid. mp 116-118. FDMS: m/e=321. α[D]589 =+100.39

Workup

  1. custombefore partitioning between diethyl ether and 1N hydrochloric acid
  2. dry with materialThe ether layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto afford 0.1818 g crude product
  6. customThe material was purified on a Chromatotron (2 mm plate, dry loaded with chloroform, eluted with 5% methanol/chloroform)

Sources & evidence

ORD record
ord-d7a36731b8d845fca5ce4699bbe5555f
Source dataset
uspto-grants-1996_08
Patent number
US05550134

Reaction notes

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