Lithium tri-s-butylborohydride → HCID 178444578, compound

HRID 1727328Notes

Reaction equation

HRID 1727328 reaction equation
[C:1]([CH:5]([CH:21]1[CH2:24][C:23](=[O:25])[CH2:22]1)[C:6]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[O:7][SiH3:8])([CH3:4])([CH3:3])[CH3:2].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1>[C:1]([CH:5]([C@@H:21]1[CH2:22][C@H:23]([OH:25])[CH2:24]1)[C:6]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[O:7][SiH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 123446256HCID 123446256, compound

Product 1

HCID 178444578HCID 178444578, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In a 50 mL flask with 3-(tert-butyl-diphenyl-siloxyethyl)cyclobutanone (0.48 g, 1.36 mmol) inside, dry THF 10 mL was added under argon to give a light yellow solution. This was cooled to −78° C., after a while, L-selectride (1.0 M in THF, 1.6 mL, 1.63 mmol) was added drop by drop and this was allowed to warm up to room temperature, after which the reaction was quenched with saturated NaHCO3 Then cool the mixture to 0° C., add 30% H2O2 drop by drop, followed by the addition of H2O and EtOAc. The organic phase was separated, washed with H2O twice and brine once, dried over MgSO4 and solvent evaporation gave the crude product, which was purified by silica gel flash chromatography (Hexane:EtOAc=9:1) to give a colorless oil (0.3 g, 61.8%). 1H NMR (CDCl3, 300 MHz): δ 1.04 (s, 9H), 1.40-2.10 (m, 5H), 2.38-2.47 (m, 2H), 3.58-3.62 (t, J=6.3, 2H), 4.04-4.14 (m, 1H), 7.34-7.45 (m, 6H), 7.64-7.67 (m, 4H).

Workup

  1. customto give a light yellow solution
  2. temperatureto warm up to room temperature
  3. customafter which the reaction was quenched with saturated NaHCO3
  4. temperatureThen cool the mixture to 0° C.
  5. additionadd 30% H2O2 drop by drop
  6. additionfollowed by the addition of H2O and EtOAc
  7. customThe organic phase was separated
  8. washwashed with H2O twice
  9. dry with materialbrine once, dried over MgSO4 and solvent evaporation
  10. customgave the crude product, which
  11. customwas purified by silica gel flash chromatography (Hexane:EtOAc=9:1)

Sources & evidence

ORD record
ord-710a57b7f6c141b1a81c99245b7db1e9
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

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