Diethyl Ether → HCID 22865070, compound

HRID 1379564Notes

Reaction equation

HRID 1379564 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.[Cl:35][C:36]1[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=1[CH:38]=[O:39]>C1COCC1>[Cl:35][C:36]1[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=1[C:38]([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:39]

Participants

8

Reactant 6

HCID 3283Diethyl EtherHCID 69962-ChlorobenzaldehydeHCID 8003PentaneHCID 11119935HCID 11119935, compoundHCID 178418306HCID 178418306, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22865070HCID 22865070, compoundYield 47%

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 50 mL of THF at -78° under an atmosphere of nitrogen was added 2.25 mL of a 1.4M solution of methyllithium in diethyl ether (3.15 mmol). After 10 min, 3.34 mL of a 1.7M solution of t-butyllithium in pentane (5.68 mmol) was added. The reaction mixture was stirred for 10 min before the addition of 2-chlorobenzaldehyde (870 mL, 7.72 mmol) as a single aliquot. The reaction was warmed to room temperature and stirred for 2 h before partitioning between ethyl acetate and 1N hydrochloric acid. The organic layer was dried, filtered and evaporated under reduced pressure to afford 1.7 g of crude product. The material was purified on a Chromatotron (4 mm plane, dry loaded with chloroform, eluted with 5% methanol/chloroform) to give 435.5 mg of desired product (47% yield): mp 105°-115°. FDMS: m/e=355, 357.

Workup

  1. custombefore partitioning between ethyl acetate and 1N hydrochloric acid
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto afford 1.7 g of crude product
  6. customThe material was purified on a Chromatotron (4 mm plane, dry loaded with chloroform, eluted with 5% methanol/chloroform)

Sources & evidence

ORD record
ord-3f5e8f32f4b642779ad10c08c4cb7156
Source dataset
uspto-grants-1997_09
Patent number
US05670514

Reaction notes

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