Piperidine → HCID 11480910, compound

HRID 2250813Notes

Reaction equation

HRID 2250813 reaction equation
CC1SC=C(/C=C(/[C@H]2[O:28][C:26](=[O:27])[CH2:25][C@H:24]([OH:29])[C:23]([CH3:31])([CH3:30])[C:21](=[O:22])[C@H:20](C)[C@@H:19](O)[C@@H](C)CCC[C@H]3O[C@H]3C2)\C)N=1.N1CCCCC1.C(Cl)Cl.CC(C)=O>C(Cl)Cl>[CH3:31][C:23]([CH3:30])([C:21](=[O:22])[CH2:20][CH3:19])[C@@H:24]([OH:29])[CH2:25][C:26]([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 448799Epothilone AHCID 21584124Propan-2-one--dichloromethane (1/1)

Product 1

HCID 11480910HCID 11480910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g (2.03 mmol) of epothilone A is dissolved in 168 mL of CH2Cl2. After adding 86 μl (0.88 mmol) of piperidine and 254 μl (0.88 mmol) of titanium tetra-isopropylate, the reaction solution is strirred for 16 h at RT. After concentration in vacuo, the product is purified by FC (200 g of silica gel, CH2Cl2→CH2Cl2/acetone=4:1) giving a colorless oil: Rf (CH2Cl2/acetone=85:15): 0.55; M+H=494.

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe product is purified by FC (200 g of silica gel, CH2Cl2→CH2Cl2/acetone=4:1)
  3. customgiving a colorless oil

Sources & evidence

ORD record
ord-41c56c16592940d48acbb9fbd3856ba4
Source dataset
uspto-grants-2008_01
Patent number
US07317100B2

Reaction notes

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