3,4-dihydro-2H-pyran → HCID 86598946, compound

HRID 2220372Notes

Reaction equation

HRID 2220372 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@H:19]([OH:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1>ClCCl.C(OCC)(=O)C.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@@H:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:26][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 24824073HCID 24824073, compound

Product 1

HCID 86598946HCID 86598946, compoundYield 107%

Reagents, catalysts & solvents 4

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl [2-(4-bromophenyl)ethyl]-[(2R)-2-hydroxy-2-phenylethyl]carbamate (3.20 g) in dichloromethane (40 ml) were added 3,4-dihydro-2H-pyran (1.28 g) and pyridinium p-toluenesulfonate (191 mg) at room temperature and the mixture was stirred at the same temperature for 5 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure to give tert-butyl [2-(4-bromophenyl)ethyl][(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]carbamate (4.11 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-187fdb01855c498597af2630825d58f8
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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