Methanol → HCID 11211254, compound

HRID 2252478Notes

Reaction equation

HRID 2252478 reaction equation
CO.[Li+].[BH4-].[CH3:5][O:6][C:7]1[CH:43]=[CH:42][C:10]([CH2:11][O:12][CH2:13][C@H:14]([CH3:41])[C@H:15]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[C@@H:16]([CH3:32])[C:17](N2[C@H](CC3C=CC=CC=3)COC2=O)=[O:18])=[CH:9][CH:8]=1.[OH-].[Na+]>C1COCC1>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][O:12][CH2:13][C@H:14]([CH3:41])[C@H:15]([O:33][Si:34]([C:37]([CH3:39])([CH3:38])[CH3:40])([CH3:35])[CH3:36])[C@@H:16]([CH3:32])[CH2:17][OH:18])=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 69213764HCID 69213764, compound

Product 1

HCID 11211254HCID 11211254, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dry MeOH (1.05 mL, 26.0 mmol) then LiBH4 (13 mL, 2.0 M solution in THF, 26 mmol) were added to a stirred solution of 20 (4.79 g, 8.62 mmol) in THF (75 mL) at 0° C. The resulting mixture was stirred at 0° C. for 45 min and at room temperature for 1 h. The solution was cooled to 0° C. and treated carefully with a 1.0 M aqueous NaOH (50 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexane/EtOAc 7:3) to give the alcohol 21 (2.98 g, 90%) as a colorless oil: IR (film) 3425, 1613, 1513, 1463, 1249, 1091, 1037 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.26 (d, J=8.5 Hz, 2H), 6.88 (d, J=8.5 Hz, 2H), 4.47 (d, J=11.7 Hz, 1H), 4.40 (d, J=11.7 Hz, 1H), 3.84 (s, 3H), 3.75 (dd, J=5.7, 2.9 Hz, 1H), 3.52 (m, 3H), 3.28 (dd, J=9.1, 7.1 Hz, 1H), 2.10 (br, 1H), 2.05 (m, 1H), 1.93-1.81 (m, 1H), 0.97 (d, J=7.0 Hz, 3H), 0.90 (s, 9H), 0.87 (d, J=7.1 Hz, 3H), 0.07 (s, 3H), 0.05 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 159.2, 130.7, 129.3, 113.8, 74.8, 72.8, 72.7, 66.3, 55.4, 39.0, 37.7, 26.2, 18.4, 15.2, 12.0, −4.1; HRMS (ESI) calcd for C18H31O3SiNa 323.2042 [M+Na]+, found 323.2035; [α]20D−0.76 (c 2.9, CHCl3).

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (hexane/EtOAc 7:3)

Sources & evidence

ORD record
ord-7e954dda4946446ca36f2a423752f667
Source dataset
uspto-grants-2008_01
Patent number
US07321046B2

Reaction notes

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