Borane → HCID 54143228, compound

HRID 1195771Notes

Reaction equation

HRID 1195771 reaction equation
[CH2:1]([N:8]1[C:14]2=[C:15]3[C:20](=[N:21][C:22]4=[CH:23][CH:24]=[CH:25][C:12](=[C:13]24)[O:11][CH2:10][C:9]1=O)[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B>O1CCCC1>[CH2:1]([N:8]1[C:14]2=[C:15]3[C:20](=[N:21][C:22]4=[CH:23][CH:24]=[CH:25][C:12](=[C:13]24)[O:11][CH2:10][CH2:9]1)[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 54287005HCID 54287005, compound

Product 1

HCID 54143228HCID 54143228, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-benzyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.71 g) in dry tetrahydrofuran (200 ml) was added borane in tetrahydrofuran (1M, 65 ml). The reaction mixture was stirred at room temperature overnight, quenched with 5% hydrochloric acid (500 ml), and stirred for an additional 2.5 hrs. The reaction mixture was cooled (0° C.), basified with 10% sodium hydroxide solution (500 ml), and extracted with ethyl acetate (800 ml). The organic phase was washed with brine, dried over anhydrous magnesium sulfate, and concentrated. Recrystallization of the residue from methanol yielded 3.05 g (68%) of product, mp 132°-133° C.

Workup

  1. customquenched with 5% hydrochloric acid (500 ml)
  2. stirringstirred for an additional 2.5 hrs
  3. temperatureThe reaction mixture was cooled (0° C.)
  4. extractionextracted with ethyl acetate (800 ml)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-60e3a02dd26b4190b391034163d50bbf
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

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