Dimethylformamide → HCID 14986489, compound

HRID 2210265Notes

Reaction equation

HRID 2210265 reaction equation
[H-].[Na+].Br[CH:4]1[C:9]([CH3:11])([CH3:10])[O:8][C:7]2[CH:12]=[CH:13][S:14][C:6]=2[CH:5]1O.[CH2:16]1[CH2:22][C:20](=[O:21])[NH:19][CH2:18][CH2:17]1.[K+].[Br-].CN(C)C=[O:28]>>[OH:28][CH:4]1[C:9]([CH3:11])([CH3:10])[O:8][C:7]2[CH:12]=[CH:13][S:14][C:6]=2[CH:5]1[N:19]1[CH2:18][CH2:17][CH2:16][CH2:22][C:20]1=[O:21]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 126652-PiperidoneHCID 24758Sodium hydride2×HCID 253877Potassium BromideHCID 149864866-bromo-5,6-dihydro-7-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran

Product 1

HCID 14986489HCID 14986489, compound

Procedure

Sodium hydride (60% in oil, 0.25 g, 6.3 mmol) was added to a solution of 6-bromo-7-hydroxy-5,6-dihydro-5,5-dimethyl-7H-thieno[3,2-b]pyran (1.5 g, 5.7 mmol) in N,N-dimethylformamide (25 mL) at 0° C. The resultant mixture was stirred at rt for 2 h. d-Valero-lactam (1.7 g, 17.1 mmol) was added to the solution followed by sodium hydride (60% in oil, 0.75 g, 18.8 mmol) and stirring was continued at rt for 4 days. The solution was poured into ice water (500 mL) and extracted with dichloromethane. The dichloromethane solution was washed with water (5×) and dried over sodium sulfate. The solvent was evaporated in vacuo and the resultant solid was triturated in diethyl ether to give the product, 0.68 g (43%): mp 151°-152° C.; IR (KBr): 3195, 1610 and 1563 cm-1 ; MS: m/z 282 (MH+); 1H NMR (CDCl3): 1.29 (s, 3H), 1.49 (s, 3H), 1.81 (m, 4H), 2.53 (t, J=6.5 Hz, 2H), 3.15 (m, 1H), 3.24 (m, 1H), 3.68 (d, J=5.0 Hz, 1H, exchanges with D2O), 3.79 (dd, J=5.0 Hz, J=9.1 Hz, 1H, simplifies to d, J=9.1 Hz with D2O), 5.84 (d, J=9.1 Hz, 1H), 6.57 (d, J=5.4 Hz, 1H) and 7.11 (d, J=5.4 Hz, 1H).

Workup

  1. additionwas added to the solution
  2. extractionextracted with dichloromethane
  3. washThe dichloromethane solution was washed with water (5×)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe resultant solid was triturated in diethyl ether
  7. customto give the product, 0.68 g (43%)

Sources & evidence

ORD record
ord-fae5a2ec7ae1466faddb34af171e6691
Source dataset
uspto-grants-1995_10
Patent number
US05457212

Reaction notes

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