Methanol → HCID 10042817, compound

HRID 1975074Notes

Reaction equation

HRID 1975074 reaction equation
Br[C:2]1[S:10][C:9]2[C@@H:8]([N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]3=[O:17])[C@H:7]([OH:18])[C:6]([CH3:20])([CH3:19])[O:5][C:4]=2[CH:3]=1.[CH2:21](N(CC)CC)C.[C]=O.[OH2:30].[CH3:31][OH:32]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:31]([C:2]1[S:10][C:9]2[C@@H:8]([N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]3=[O:17])[C@H:7]([OH:18])[C:6]([CH3:20])([CH3:19])[O:5][C:4]=2[CH:3]=1)([O:32][CH3:21])=[O:30]

Participants

7

Reactant 5

HCID 887MethanolHCID 962WaterHCID 8471TriethylamineHCID 10067049HCID 10067049, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 10042817HCID 10042817, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

A solution of trans-2-bromo-5,6-dihydro-6-hydroxy-5,5-dimethyl -7-(2-oxopiperidin-1-yl)-7H-thieno[3,2-b]pyran (1.35 g, 3.75 mmol), triethylamine (0.87 mL, 6.25 mmol) and bis(triphenylphosphine)-palladium(II) chloride (80 mg, 0.11 mmol) in methanol (120 mL) was heated in a stainless steel Parr pressure reactor pressurized with carbon monoxide (160 psi) at 100° C. for four days. The resultant solution was poured into water and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo. The product was purified by flash chromatography using 2% methanol in dichloromethane as the eluant to give the product, 0.83 g (65%) as a colorless solid: mp 104°-106° C.; IR(KBr): 1718, 1618 and 1565 cm-1 ; MS: m/z 340MH+); 1H NMR(CDCl3): δ 1.29 (s, 3H), 1.49 (s, 3H), 1.43 (m, 4H), 2.53 (m, 2H), 3.14 (m, 1H), 3.23 (m, 1H), 3.52 (d, J=5.4 Hz, 1H, exchanges with D2O), 3.81 (d,d, J=5.4 Hz, J=9.5 Hz, 1H, simplifies to d, J=9.5 Hz, with D2O), 3.86 (s, 3H), 5.87 (d, J=9.5 Hz, 1H) and 7.24 (s, 1H).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe product was purified by flash chromatography
  5. customto give the product, 0.83 g (65%) as a colorless solid

Sources & evidence

ORD record
ord-45104b74ccea4d0187d4c4a96916db69
Source dataset
uspto-grants-1994_02
Patent number
US05284857

Reaction notes

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