3,4-dihydro-2H-pyran → HCID 19019548, compound

HRID 1109759Notes

Reaction equation

HRID 1109759 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:24]([N:31]1[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33][CH2:32]1)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>C(Cl)Cl>[C:24]([N:31]1[CH2:36][CH2:35][CH:34]([O:37][CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][O:1]2)[CH2:33][CH2:32]1)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 19019548HCID 19019548, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

With stirring, 8.16 ml (0.09 mol) of 3,4-dihydro-2H-pyran and 1.5 g (0.006 mol) of pyridinium-(toluene-4-sulfonate) are added to a solution of 12.08 g (0.06 mol) of N-BOC-4-hydroxypiperidine (cf. EP 0 278 621) in 300 ml of methylene chloride. The reaction mixture is stirred for 2.5 hours at room temperature, then washed with 2×50 ml of brine:water (1:1) mixture, dried over sodium sulfate and concentrated under vacuum, giving the title compound in the form of a colourless oil; Rf =0.58 (silica gel/ethyl acetate:hexane (2:1), which gradually solidifies in crystalline form at 0° C.

Workup

  1. stirringThe reaction mixture is stirred for 2.5 hours at room temperature
  2. washwashed with 2×50 ml of brine:water (1:1) mixture
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fb9ecb06ab2747a0b6f629a12796fe8c
Source dataset
uspto-grants-1994_06
Patent number
US05322852

Reaction notes

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