Tributylstannane → 4-Benzoyloxy-1-(2-hydroxycyclohexyloxy)-2,2,6,6-tetramethylpiperidine

HRID 843471

Reaction equation

HRID 843471 reaction equation
C([SnH](CCCC)CCCC)CCC.Br[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[OH:21].[C:22]([O:30][CH:31]1[CH2:36][C:35]([CH3:38])([CH3:37])[N:34]([OH:39])[C:33]([CH3:41])([CH3:40])[CH2:32]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCCCCCC>ClC1C=CC=CC=1.CCCCCCC.C(OCC)(=O)C>[C:22]([O:30][CH:31]1[CH2:32][C:33]([CH3:40])([CH3:41])[N:34]([O:39][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[OH:21])[C:35]([CH3:38])([CH3:37])[CH2:36]1)(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 5948TributylstannaneHCID 8900HeptaneHCID 2664112-BromocyclohexanolHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 225076454-Benzoyloxy-1-(2-hydroxycyclohexyloxy)-2,2,6,6-tetramethylpiperidine

Reagents, catalysts & solvents 2

HCID 7964ChlorobenzeneSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

Tributyltin hydride is added dropwise to a solution of 2-bromocyclohexanol and excess 4-benzoyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine in chlorobenzene. The mixture is heated to facilitate reaction. The crude reaction mixture is passed through silica gel with heptane and then heptane/ethyl acetate to afford the title compound as a mixture of cis/trans isomers.

Workup

  1. temperatureThe mixture is heated
  2. customreaction
  3. customThe crude reaction mixture

Sources & evidence

ORD record
ord-dea195a2f22a4c0c902aa4d5569c65d2
Source dataset
uspto-grants-2002_04
Patent number
US06376584B1

Linked notes

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