Borane;tetrahydrofuran → HCID 22139447, compound

HRID 1825791Notes

Reaction equation

HRID 1825791 reaction equation
[CH2:1]([O:8][C:9]1[C:22]2[S:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=O)[C:13]=2[C:12]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1.CC(C)=O.C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:22]2[S:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][C:13]=2[C:12]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 22139400HCID 22139400, compound

Product 1

HCID 22139447HCID 22139447, compoundYield 99.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) suspension of 4-benzyloxy-1-(4-methoxy-benzylamino)-thioxanthen-9-one (8.16 g, 18.00 mmol) in dry THF (150 ml) was added Borane-THF complex (90 mmol, 90 ml 1M in THF) in a dropwise fashion. The reaction was allowed to slowly warm to room temperature and stirred for a further 16 hours to give a homogeneous yellow solution. To mixture was then cooled (0° C.) and diluted slowly with acetone (150 ml) and then stirred for 60 minutes at room temperature. The solvent was removed in vacuo to give a crude residue that was diluted in CH2Cl2 (100 ml) and the washed with a saturated solution of NaHCO3 (100 ml), dried using MgSO4, filtered and concentrated in vacuo to give the title compound as a mild amber oil (7.90 g, 99.8%) m/z (LC-MS, ESP): 438 [M+H]+, R/T=5.01 mins.

Workup

  1. temperatureTo a cooled
  2. customto give a homogeneous yellow solution
  3. temperatureTo mixture was then cooled (0° C.)
  4. stirringstirred for 60 minutes at room temperature
  5. customThe solvent was removed in vacuo
  6. customto give a crude residue that
  7. washthe washed with a saturated solution of NaHCO3 (100 ml)
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee6e947d05084e5a99733332068947e4
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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