Toluene → HCID 69601022, compound

HRID 2215090Notes

Reaction equation

HRID 2215090 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14])[C@@H:5](/[CH:15]=[CH:16]/[C:17](=[O:25])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:4][S:3]1.C1(C)C=CC=CC=1.[B]1OC2C(=CC=CC=2)O1>C(Cl)Cl>[OH:25][CH:17]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)/[CH:16]=[CH:15]/[C@H:5]1[CH2:4][S:3][C:2](=[O:1])[N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6327445BenzcatechinboraneHCID 69601012HCID 69601012, compound

Product 1

HCID 69601022HCID 69601022, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a solution of 4-3 (0.15 g, 0.4 mmol) in 8 mL CH2Cl2 was added 1M (R)-CBS in toluene (0.45 mL, 0.45 mmol) and cooled to −40° C. to which a solution of catechol borane (0.13 mL, 1.2 mmol) in CH2Cl2 (1 mL) was added dropwise. The solution was stirred at −40° C. for one hour and allowed to warm up to −20° C. during the following two hours. The reaction mixture was quenched at −20° C. with 1 N HCl and was stirred for 4 hours at room temperature. The phases were separated and the organic phase was sequentially washed with 1N HCl, H2O, 1 N NaOH, brine and dried over Na2SO4, filtered and concentrated in vacuo. The compound was purified by flash chromatography using 40–50% ethyl acetate/hexanes to yield 125 mg of 4-4 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.37–7.21 (m, 5H), 5.84 (dd, 1H), 5.65 (dd, 1H), 4.46 (q, 1H), 4.22 (q, 1H), 3.86–3.35 (m, 2H), 2.97 (dd, 1H), 2.88 (m, 2H), 2.80 (m, 1H), 2.36 (t, 2H), 1.70–1.27 (m, 8H); MS (+ESI): m/z 359.0 (M+1)+.

Workup

  1. additionwas added dropwise
  2. temperatureto warm up to −20° C. during the following two hours
  3. customThe reaction mixture was quenched at −20° C. with 1 N HCl
  4. stirringwas stirred for 4 hours at room temperature
  5. customThe phases were separated
  6. washthe organic phase was sequentially washed with 1N HCl, H2O, 1 N NaOH, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-821dc804310c43b79845a09294983c3a
Source dataset
uspto-grants-2006_09
Patent number
US07109223B2

Reaction notes

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