Bromine → HCID 14986503, compound

HRID 257214Notes

Reaction equation

HRID 257214 reaction equation
[OH:1][CH:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][S:12][C:4]=2[CH:3]1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[O:19].[Br:20]Br>ClCCl>[Br:20][C:11]1[S:12][C:4]2[CH:3]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3=[O:19])[CH:2]([OH:1])[C:7]([CH3:8])([CH3:9])[O:6][C:5]=2[CH:10]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 14986489HCID 14986489, compound

Product 1

HCID 14986503HCID 14986503, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in Example 4 starting with 5,6-dihydro-6-hydroxy-5,5-dimethyl-7-(2-oxopiperidin-1-yl)-7H-thieno[3,2-b]pyran (1.4 g, 5.0 mmol) and bromine (0.27 mL, 5.2 mmol) in dichloromethane (30 mL). Purification by flash chromatography using 1% methanol in dichloromethane as the eluant and recrystallization from dichloromethane/hexanes gave the product, 3.87 g (78%), as a colorless solid: mp 200°-202° C.; IR(KBr): 3442, 2942, 1616, 1571 and 1488 cm-1 ; MS: m/z 360 (MH+); 1H NMR(CDCl3): δ 1.29 (s, 3H), 1.46 (s, 3H), 1.82 (m, 4H), 2.51 (m, 2H), 3.12 (m, 1H), 3.27 (m, 1H), 3.46 (d, J=5.0 Hz, 1H, exchanges with D2O),3.78 (d,d, J=9.0 Hz, J=5.0 Hz, 1H, simplifies to d, J=9.0 Hz, with D2O), 5.74 (d, J=9.0 Hz, 1H) and 7.58 (s, 1H).

Workup

  1. customPurification by flash chromatography
  2. customas the eluant and recrystallization from dichloromethane/hexanes
  3. customgave the product, 3.87 g (78%)

Sources & evidence

ORD record
ord-1656e296ac754851a3c7f91e9a02c4a0
Source dataset
uspto-grants-1993_11
Patent number
US05260453

Reaction notes

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