Sodium ethanethiolate → HCID 59124153, compound

HRID 1760636Notes

Reaction equation

HRID 1760636 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:7][CH:6]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[C:16]([O:17]C)[C:10]=3[CH:9]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C@H:20]([OH:33])[CH2:21][O:22][C:23]1[C:28]2[CH:29]=[C:30]([CH3:32])[O:31][C:27]=2[CH:26]=[CH:25][CH:24]=1.C([S-])C.[Na+]>CN(C=O)C>[CH3:1][C:2]1([CH3:34])[CH2:7][CH:6]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:10]=3[CH:9]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C@H:20]([OH:33])[CH2:21][O:22][C:23]1[C:28]2[CH:29]=[C:30]([CH3:32])[O:31][C:27]=2[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 59124152HCID 59124152, compound

Product 1

HCID 59124153HCID 59124153, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2S)-(+)-3-[2,2-dimethyl-4-(4-methoxybenzo[b]thiophen-2-yl)piperidin-1-yl]-1-(2-methylbenzofuran-4-yl)oxy-2-propanol (0.750 g, 1.56 mmol) and sodium ethanethiolate (2.10 g, 25.0 mmol) in DMF (26 mL) was heated at 90° C. for 14 h and concentrated under reduced pressure. The residue was then diluted with 50 mL of brine and extracted with CH2Cl2 (3×50 mL). The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography [0 to 6% (2.0 M NH3 in MeOH)/CH2Cl2]. The residual DMF was removed as an azeotrope with xylenes and re-run through a column of silica gel [3.5% (2.0 M NH3 in MeOH)/CH2Cl2] to give the title compound as an off-white foam (0.2751 g, 37%). IR (KBr) 3593, 2969, 2936, 1281, 1085 cm−1. Ion Spray MS 466.2 (M+H)+; 464.3 (M−H)−. [α]D=55.26 (c 0.5791, MeOH). C27H31NO4S.0.2CH2Cl2

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was then diluted with 50 mL of brine
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography [0 to 6% (2.0 M NH3 in MeOH)/CH2Cl2]
  8. customThe residual DMF was removed as an azeotrope with xylenes

Sources & evidence

ORD record
ord-887634bed91b4855a214472dc277b791
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

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