Tetrahydrofuran → HCID 53736249, compound

HRID 343699Notes

Reaction equation

HRID 343699 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([CH2:34][CH2:35][N:36]3[CH2:41][CH2:40][C:39]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:42]([NH2:44])=[O:43])[CH2:38][CH2:37]3)[CH2:19][CH2:18][N:17]([C:20](=[O:33])[C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=3)[CH2:16]2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2([CH2:34][CH2:35][N:36]3[CH2:37][CH2:38][C:39]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)([C:42]([NH2:44])=[O:43])[CH2:40][CH2:41]3)[CH2:19][CH2:18][N:17]([C:20](=[O:33])[C:21]3[CH:22]=[C:23]([O:31][CH3:32])[C:24]([O:29][CH3:30])=[C:25]([O:27][CH3:28])[CH:26]=3)[CH2:16]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 54486321HCID 54486321, compound

Product 1

HCID 53736249HCID 53736249, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 1-[2-[3-[4-(tert-butyldimethylsilyloxy)-phenyl]-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl -piperidine-4-carboxylic acid amide (6 mmol) and THF (20 mL). Cool using an ice bath. Add a 1M THF solution of tetrabutylammonium fluoride (7 mL) in dropwise fashion. After 30 minutes, concentrate in vacuo to obtain a residue. Add dichloromethane (50 mL) to the residue. Extract with water (3×15 mL), dry over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Purify to obtain the title compound.

Workup

  1. temperatureCool
  2. concentrationconcentrate in vacuo
  3. customto obtain a residue
  4. extractionExtract with water (3×15 mL)
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customto obtain a residue
  9. customPurify

Sources & evidence

ORD record
ord-539361dc2d3e4f09add74d41506675f8
Source dataset
uspto-grants-1999_01
Patent number
US05861416

Reaction notes

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