Toluene → HCID 13080730, compound

HRID 1746813Notes

Reaction equation

HRID 1746813 reaction equation
C1(C)C=CC=CC=1.[CH3:8][Si:9]([CH3:32])([C:28]([CH3:31])([CH3:30])[CH3:29])[O:10][CH2:11][C@@H:12]1[C@@H:19]2[C@@H:15]([O:16][C:17](=[O:20])[CH2:18]2)[CH2:14][C@H:13]1[O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>O.CO>[CH3:8][Si:9]([CH3:32])([C:28]([CH3:30])([CH3:29])[CH3:31])[O:10][CH2:11][C@@H:12]1[C@@H:19]2[C@@H:15]([O:16][CH:17]([OH:20])[CH2:18]2)[CH2:14][C@H:13]1[O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 24436Sodium SulfateHCID 13080724(3aR,4S,5R,6aS)-4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-5-[(oxan-2-yl)oxy]hexahydro-2H-cyclopenta[b]furan-2-oneHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 13080730HCID 13080730, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

An anhydrous toluene (315 mL) solution of the compound 1 (68.4 g) was cooled to around −60° C. in a dry ice-methanol bath, and then a diisobutyl aluminum hydride/toluene solution (0.99M, 209 mL) was added dropwise over 33 minutes. The mixture was stirred for 2 hours, and then to the reaction mixture was added dropwise methanol (3.2 mL) at −65° C. over 3 minutes to stop the reaction. The reaction liquid was raised to around 0° C., and water was then added dropwise in two parts (18.5 mL+18 mL) while the mixture was stirred. Thereto was added anhydrous sodium sulfate (7.4 g), and the mixture was stirred at room temperature for 1 hour, and filtered with Celite (trade name). The solid that was filtered off was washed with tetrahydrofuran (160 mL), and concentrated to obtain a titled compound (70.7 g) having the following physical property values.

Workup

  1. customthe reaction
  2. customThe reaction liquid
  3. stirringwas stirred
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. filtrationfiltered with Celite (trade name)
  6. filtrationThe solid that was filtered off
  7. washwas washed with tetrahydrofuran (160 mL)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-522c256eaa23458292227c4446668319
Source dataset
uspto-grants-2015_10
Patent number
US09150537B2

Reaction notes

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