Diethyl Ether → HCID 178517709, compound

HRID 1609114Notes

Reaction equation

HRID 1609114 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C@H:12]3[CH2:16][C@:5]([C:17]([N:19]4[CH2:24][CH2:23][CH:22]([CH2:25][C:26]5[C:27]([O:32]C)=[N:28][CH:29]=[CH:30][CH:31]=5)[CH2:21][CH2:20]4)=O)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1.B(F)(F)F.CCOCC.O1CCCC1.B.C(OCC)C>O1CCCC1.Cl.CO>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C@H:12]3[CH2:16][C@:5]([CH2:17][N:19]4[CH2:24][CH2:23][CH:22]([CH2:25][C:26]5[C:27]([OH:32])=[N:28][CH:29]=[CH:30][CH:31]=5)[CH2:21][CH2:20]4)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 8000Boron trifluoride etherateHCID 2723981Borane;tetrahydrofuranHCID 57261037HCID 57261037, compound

Product 1

HCID 178517709HCID 178517709, compoundYield 66.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-((9S,10S)-2-chloro-9,10-dihydro-9,10-methanoanthracen-9-ylcarbonyl)-4-(2-methoxy-3-pyridylmethyl)piperidine (1.80 g. 3.92 mmol) in tetrahydrofuran (50 mL) was treated with boron trifluoride etherate (612 mg, 4.31 mmol) and borane- tetrahydrofuran (14.9 mL of a 1.0M solution, 14.9 mmol). The resulting solution was heated to reflux for 3 h. The mixture was then concentrated on a rotary evaporator to give a colorless residue. The residue was dissolved in concentrated hydrochloric acid (50 mL, 12N) and heated to reflux for 3 h. The solution was concentrated to dryness on a rotary evaporator to give a glassy residue. This residue was dissolved in methanol (100 mL) and concentrated to dryness on a rotary evaporator (3X) to give a white foam. This foam was dissolved in methanol (5 mL) and added to rapidly stirred diethyl ether (200 mL) to give a white precipitate which was collected and washed with diethyl ether to give the hydrochloride salt of the title compound (1.3 g, 2.60 mmol, 66%) as an off-white powder, mp 211°-215° C.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 3 h
  3. concentrationThe mixture was then concentrated on a rotary evaporator
  4. customto give a colorless residue
  5. temperatureheated
  6. temperatureto reflux for 3 h
  7. concentrationThe solution was concentrated to dryness on a rotary evaporator
  8. customto give a glassy residue
  9. concentrationconcentrated to dryness on a rotary evaporator (3X)
  10. customto give a white foam
  11. customto give a white precipitate which
  12. customwas collected
  13. washwashed with diethyl ether

Sources & evidence

ORD record
ord-7650907bfb9548d2b6a24c713c019961
Source dataset
uspto-grants-1995_03
Patent number
US05399568

Reaction notes

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