Tetrahydrofuran → HCID 131720251, compound

HRID 2288270Notes

Reaction equation

HRID 2288270 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, 1.0 M 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, 3 M) 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 (CDCl2) δ1.10 (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, CH2CH2CH2OH); 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, 3 M) 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-bf6adba7c3194d2c958a5e2396bdf878
Source dataset
uspto-grants-2000_07
Patent number
US06087482

Reaction notes

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