Water → HCID 18951279, compound

HRID 1965152Notes

Reaction equation

HRID 1965152 reaction equation
[BH4-].[Na+].O.[C:4]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:13][CH:12]1[CH:24]=[CH:25][N+:26]([O-:28])=[O:27])=[O:10])([CH3:7])([CH3:6])[CH3:5]>C1COCC1>[C:4]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][Si:17]([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18])[CH2:13][CH:12]1[CH2:24][CH2:25][N+:26]([O-:28])=[O:27])=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67212929HCID 67212929, compound

Product 1

HCID 18951279HCID 18951279, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

A 1 L round-bottomed flask was charged with NaBH4 (3.2 g, 84.5 mmol) in THF (300 mL) and then cooled to −20° C. Water (50 mL) was added to the reaction mixture followed by the dropwise addition of 2 (6.3 g, 16.9 mmol) in THF (50 mL) over 1 h. After an additional 30 min, the cold reaction mixture was quenched by the careful addition of 1M HCl (60 mL). The reaction mixture was then diluted with EtOAc. The organic phase was washed successively with 1M HCl and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was chromatographed by flash silica gel chromatography (4:1 hexanes/EtOAc) to afford 5.9 g (93%) of 3. 1H NMR (CDCl3, 300 MHz), mixture of rotomers: δ4.48 (m, 1H), 4.32 (m, 1H), 4.08 (m, 1H), 3.55 (m, 0.4H), 3.38 (m, 0.6H), 3.28 (app dd, J=11.7, 4.2 Hz, 1H), 2.32 (m, 1H), 2.18 (m, 1H), 2.04 (m, 2H), 1.67 (m, 1H), 1.45 (s, 9H), 0.85 (s, 9H), 0.05 (s, 6H) ppm.

Workup

  1. customthe cold reaction mixture
  2. customwas quenched by the careful addition of 1M HCl (60 mL)
  3. additionThe reaction mixture was then diluted with EtOAc
  4. washThe organic phase was washed successively with 1M HCl and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was chromatographed by flash silica gel chromatography (4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-5de3fc59410e4df0ab6e8d58900f3620
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

Loading…