Delta-Valerolactone → HCID 19010457, compound

HRID 1741598Notes

Reaction equation

HRID 1741598 reaction equation
Br[C:2]1[S:10][C:9]2[CH2:8][CH2:7][N:6]([CH2:11][CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[C:5](=[O:26])[C:4]=2[CH:3]=1.[Li]CCCC.[C:32]1(=[O:38])[O:37][CH2:36][CH2:35][CH2:34][CH2:33]1>C1COCC1>[OH:38][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([C:2]1[S:10][C:9]2[CH2:8][CH2:7][N:6]([CH2:11][CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[C:5](=[O:26])[C:4]=2[CH:3]=1)=[O:37]

Participants

5

Reactant 3

HCID 10953Delta-ValerolactoneHCID 105512282-Bromo-4-oxo-5-[2-(N-BOC-4-piperidinyl)ethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridineHCID 178418339Butyllithium

Product 1

HCID 19010457HCID 19010457, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-1 (0.66 g, 1.5 mmoles) in THF (30 ml) was cooled to -78° and treated with n-BuLi (3.0 mmoles) and the resulting yellow brown solution was stirred for 30 minutes. Then, valerolactone (0.16 g, 1.65 mmoles) was added and this was stirred at -70° for 6 hours and then overnight at ambient temperature. The reaction mixture was cooled to -10°, quenched with 10% KHSO4 and concentrated. The residue was taken up in H2O/EtOAc and the organic phase was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on silica gel eluting with hexane (3)/acetone(2) to give 4-1, Rf 0.35.

Workup

  1. stirringthis was stirred at -70° for 6 hours
  2. customovernight
  3. customat ambient temperature
  4. temperatureThe reaction mixture was cooled to -10°
  5. customquenched with 10% KHSO4
  6. concentrationconcentrated
  7. washthe organic phase was washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography on silica gel eluting with hexane (3)/acetone(2)
  11. customto give 4-1, Rf 0.35

Sources & evidence

ORD record
ord-beb6c4257c04482d9fc04fd9c181b193
Source dataset
uspto-grants-1994_08
Patent number
US05334596

Reaction notes

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