HCID 54031872, compound → HCID 57080220, compound

HRID 1167929Notes

Reaction equation

HRID 1167929 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][C@H:8]([CH2:12][C@H:13]([CH3:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:9](O)=[O:10])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6](=[O:20])[CH2:7][C@@H:8]([CH2:9][OH:10])[CH2:12][C@H:13]([CH3:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 54031872HCID 54031872, compound

Product 1

HCID 57080220HCID 57080220, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 157 (3.52 g, 12.3 mmol) was dissolved in anhydrous THF (123 mL) and cooled to 0° C. Borane dimethylsulfide complex (10 M, 3.69 mL) was added dropwise, and the reaction then warmed to room temperature and stirred for 1 hour. The reaction was cooled to 0° C., and quenched with MeOH (20 mL) added dropwise. The reaction was stirred for 18 hours, and the solvent rotovapped off. The crude material was chromatographed on silica eluting with 20% EtOAc/hexanes to give 158 (2.28 g, 68%) as an oil. 1H NMR (400 MHz, CDCl3) δ 3.65-3.59 (m, 1H), 3.43 (dd, J=11.1, 6.96 Hz, 1H), 2.31 (dd, J=14.9, 7.57 Hz, 1H), 2.21 (dd, J=15.1, 5.62 Hz, 1H), 2.06-2.02 (m, 1H), 1.43 (s, 9H), 1.40-1.25 (m, 4H), 1.07-1.13 (m, 1H), 1.03-0.96 (m, 1H), 0.86-0.84 (m, 6H); MS (APCI) m/z 216 (M+−56, 100%).

Workup

  1. additionBorane dimethylsulfide complex (10 M, 3.69 mL) was added dropwise
  2. customthe reaction
  3. temperaturethen warmed to room temperature
  4. temperatureThe reaction was cooled to 0° C.
  5. customquenched with MeOH (20 mL)
  6. additionadded dropwise
  7. stirringThe reaction was stirred for 18 hours
  8. customThe crude material was chromatographed on silica eluting with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-85cb25ce4dbc45bc9d5aaffbf9a56a21
Source dataset
uspto-grants-2003_09
Patent number
US06620829B2

Reaction notes

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