1,2-Dichloroethane → HCID 59264803, compound

HRID 646473Notes

Reaction equation

HRID 646473 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[O:28][N:27]=[C:26]([CH3:29])[C:25]=1[C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH:33]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.ClCCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[O:28][N:27]=[C:26]([CH3:29])[C:25]=1[C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydride2×HCID 59264723HCID 59264723, compound

Product 1

HCID 59264803HCID 59264803, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-[5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-3-methyl-isoxazol-4-yl]-benzaldehyde (25 mg, 0.05 mmol) and morpholine (0.3 ml) were mixed with DCE (0.5 ml) in an microwave tube. Sodium triacetoxyborohydride (15 mg, 1.4 equiv) was added, the tube sealed, and nitrogen atmosphere introduced. After 1 hr more sodium triacetoxyborohydride (15 mg) was added and the reaction left stirring overnight. TLC analysis showed that the reaction had not gone to completion so a drop of acetic acid was added and the reaction again left stirring overnight after which the reaction was quenched with 1M NaHCO3 solution (7 ml) and extracted into EtOAc (5 ml). This was dried over MgSO4 and the solvent removed in vaccuo to provide 13 mg of the crude product as an off white powder which was taken over to the deprotection step.

Workup

  1. customthe tube sealed
  2. additionnitrogen atmosphere introduced
  3. waitthe reaction left
  4. additionwas added
  5. customthe reaction
  6. waitagain left
  7. stirringstirring overnight after which the reaction
  8. customwas quenched with 1M NaHCO3 solution (7 ml)
  9. extractionextracted into EtOAc (5 ml)
  10. dry with materialThis was dried over MgSO4
  11. customthe solvent removed in vaccuo

Sources & evidence

ORD record
ord-1ed443573fb24e7ba199e62e3fc48f87
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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