Nitric Acid → 1-(6-Hydroxy-5,5-dimethyl-2-nitro-6,7-dihydro-5H-thieno[3,2-b]pyran-7-yl)piperidin-2-one

HRID 981496Notes

Reaction equation

HRID 981496 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].[N+:20]([O-])([OH:22])=[O:21].[K+].[Br-]>C(O)(=O)C>[OH:1][CH:2]1[C:7]([CH3:8])([CH3:9])[O:6][C:5]2[CH:10]=[C:11]([N+:20]([O-:22])=[O:21])[S:12][C:4]=2[CH:3]1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[O:19]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 253877Potassium BromideHCID 14986489HCID 14986489, compound

Product 1

HCID 1838031-(6-Hydroxy-5,5-dimethyl-2-nitro-6,7-dihydro-5H-thieno[3,2-b]pyran-7-yl)piperidin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared as described in Example 5 starting with 5,6-dihydro-6-hydroxy-5,5-dimethyl-7(2-oxopiperidin-1-yl)-7H-thieno[3,2-b]pyran (1.5 g, 5.33 mmol) and 90% nitric acid (2.5 mL) in acetic acid (25 mL) to give the product, 0.837 g (48%), as a yellow solid: mp 210°-211° C.; IR (KBr): 3231, 1613, 1515 and 1492 cm-1 ; MS: m/z 327 (MH+); 1H NMR (CDCl3): δ 1.32 (s, 3H), 1.51 (s, 3H), 1.84 (m, 4H), 2.55 (m, 2H), 3.20 (m, 2H), 3.84 (d, J=9.5 Hz, 1H), 4.78 (bs, 1H, exchanges with D2O), 5.86 (d, J=9.5 Hz, 1H) and 7.40 (s, 1H). Anal. Calcd. for C14H18N2O5S: C, 51.52; H, 5.56; N, 8.58; S, 9.86.

Workup

  1. customto give the product, 0.837 g (48%)

Sources & evidence

ORD record
ord-61067b8d73bc4b4685088c62d0d2817a
Source dataset
uspto-grants-1991_02
Patent number
US04992435

Reaction notes

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