3-Pyridinemethanol → HCID 18727250, compound

HRID 1856862Notes

Reaction equation

HRID 1856862 reaction equation
C(P(CCCC)CCCC)CCC.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][N:24]([S:27]([NH:30][C@H:31]([CH:36]([CH3:38])[CH3:37])[C:32]([O:34][CH3:35])=[O:33])(=[O:29])=[O:28])[CH2:23][CH2:22]2)=[CH:17][CH:16]=1.[N:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45]O)[CH:40]=1>C1C=CC=CC=1>[N:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][N:30]([S:27]([N:24]2[CH2:25][CH2:26][CH:21]([C:18]3[CH:19]=[CH:20][C:15]([Br:14])=[CH:16][CH:17]=3)[CH2:22][CH2:23]2)(=[O:28])=[O:29])[C@H:31]([CH:36]([CH3:38])[CH3:37])[C:32]([O:34][CH3:35])=[O:33])[CH:40]=1

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 13831TributylphosphineHCID 18727236HCID 18727236, compound

Product 1

HCID 18727250HCID 18727250, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tri-n-butylphosphine (0.37 ml, 1.5 mmol) was added to a solution of methyl 2-(R)-{[4-(4-bromophenyl)piperidine-1-sulfonyl]amino}-3-methylbutyrate (560 mg, 1.25 mmol), 3-pyridylcarbinol (0.15 ml, 1.5 mmol), and 1,1'-(azodicarbonyl)piperidine (377 mg, 1.5 mmol) in benzene (30 ml). After stirring at RT for 48 h, the reaction mixture was concentrated and the residue was triturated with ether (60 ml). After filtering off the solids, the ether layer was concentrated in vacuo and the residue was chromatographed (SiO2, 40% ethyl acetate/hexane) to give methyl 2-(R)-{(pyridin-3-ylmethyl)-[4-(4-bromophenyl)piperidine-1-sulfonyl]amino}-3-methylbutyrate as a colorless oil (41%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was triturated with ether (60 ml)
  3. filtrationAfter filtering off the solids
  4. concentrationthe ether layer was concentrated in vacuo
  5. customthe residue was chromatographed (SiO2, 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-be8b6eb282994dbd93857e0a8f72d49e
Source dataset
uspto-grants-2000_11
Patent number
US06143744

Reaction notes

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