Tetrahydrofuran → HCID 131720251, compound

HRID 1489462Notes

Reaction equation

HRID 1489462 reaction equation
[CH2:1]([O:8][CH2:9][C@@:10]1([N:37]2[CH:45]=[C:43]([CH3:44])[C:41](=[O:42])[NH:40][C:38]2=[O:39])[O:33][C@H:13]([CH2:14][O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:12]([CH2:34][CH:35]=[CH2:36])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C[O:49]CC1>>[CH2:1]([O:8][CH2:9][C@@:10]1([N:37]2[CH:45]=[C:43]([CH3:44])[C:41](=[O:42])[NH:40][C:38]2=[O:39])[O:33][C@H:13]([CH2:14][O:15][Si:16]([C:29]([CH3:30])([CH3:32])[CH3:31])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C@@H:12]([CH2:34][CH2:35][CH2:36][OH:49])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 131720250HCID 131720250, compound

Product 1

HCID 131720251HCID 131720251, compoundYield 44.3%

Conditions

Temperature
23 °C

Procedure

BH3 (2.7 mL, 1.0M solution in THF) was added to a solution of 18 (1.12 g, 1.8 mmol) in THF (15 ml) followed by stirring for 3 hr at 23° C. The reaction was quenched by the slow addition of MeOH (0.2 mL). A NaOH solution (6 mL, 3M) was added and the reaction mixture concentrated under reduced pressure to a white solid. The solid was suspended in THF (15 mL) and oxidized by the addition of H2O2 (3 mL, 30% aqueous solution) for 3 hr at 23° C. The solvent was evaporated under reduced pressure and the residue purified by silica gel chromatography (CH2Cl2 /AcOEt, 10:1 then 3:1) to give 0.51 g (44.3%) of the title compound as a white foam. 1H NMR (CDCl3) δ 1.10 (s, 9H, Me3C); 1.18-1.54 (m, 4H); 1.65 (s, 3H, 5-CH3); 2.10-2.40 (m, 3H); 2.18 (t, 1H, J=5.7 Hz, OH); 3.62 (m, 2H, CH2CH2 CH2OH); 3.65 (m, 2H, 5'-H); 4.07 (d, 1H, J=9.8 Hz, 4'-H); 4.71 (s, 2H, OCH2Ph), 5.50 (s, 2H, NCH2O); 6.11 (t, 1H, J=5.1 Hz, 1'-H); 7.26-7.51 (m, 12H, 6-H and aromatic-H); and 7.67-7.70 (m, 4H, aromatic-H).

Workup

  1. customThe reaction was quenched by the slow addition of MeOH (0.2 mL)
  2. additionA NaOH solution (6 mL, 3M) was added
  3. concentrationthe reaction mixture concentrated under reduced pressure to a white solid
  4. additionoxidized by the addition of H2O2 (3 mL, 30% aqueous solution) for 3 hr at 23° C
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue purified by silica gel chromatography (CH2Cl2 /AcOEt, 10:1

Sources & evidence

ORD record
ord-a799b710218d47f2bb23dc240ec65536
Source dataset
uspto-grants-1997_10
Patent number
US05677437

Reaction notes

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