Acetic Acid → HCID 66758909, compound

HRID 917050Notes

Reaction equation

HRID 917050 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][C:10](=[C:18]=[CH:19][CH:20]=O)[C:11]3[C:12]([O:17][C:7]=2[CH:6]=[CH:5][CH:4]=1)=[N:13][CH:14]=[CH:15][CH:16]=3.[C:22](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2([OH:49])[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)=[CH:39][CH:38]=1.C(O)(=O)C>ClCCl.C(OCC)(=O)C.O>[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2([OH:49])[CH2:44][CH2:45][N:46]([C:20]([CH2:19][CH:18]=[C:10]3[C:11]4[C:12](=[N:13][CH:14]=[CH:15][CH:16]=4)[O:17][C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=4[CH2:9]3)=[CH2:22])[CH2:47][CH2:48]2)=[CH:39][CH:38]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86585734HCID 86585734, compound

Product 1

HCID 66758909HCID 66758909, compoundYield 69.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of step 1 (90 mg) in dichloromethane (6 ml) were added sodium triacetoxyborohydride (170 mg), 4-(4-chlorophenyl)-4-hydroxypiperidine (70 mg) and acetic acid (0.02 ml) and the mixture stirred at room temperature for 24 hour. Water and ethyl acetate were added to the reaction mixture, the organic layer was separated and washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with dichloromethane-methanol (95:5) to give 4-(4-chlorophenyl)-1-[4-(5,11-dihydro-7-methoxy[1]benzoxepino[2,3-b]pyridin-5-ylidene)buten-2-yl]piperidin-4-ol (110 mg).

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried with magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with dichloromethane-methanol (95:5)

Sources & evidence

ORD record
ord-234d33e26ab34b44895b1628eb7cb16e
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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