p-Toluenesulfonic acid → HCID 10998648, compound

HRID 1392087Notes

Reaction equation

HRID 1392087 reaction equation
C(=O)(OC)O[CH2:3]/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[CH2:15]([NH:22][C@H:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:4]=[CH2:3])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7504BenzylamineHCID 10035469HCID 10035469, compound

Product 1

HCID 10998648HCID 10998648, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-cinnamyl methyl carbonate (0.50 g) in THF (10 mL) at RT under N2 was added the (S)-(1,1′-Dinaphthyl-2,2′-di-(S,S)-1-phenylethylphosphoramidite* (0.140 g), [Ir(COD)Cl]2 (0.035 g) and benzylamine (0.557 g). The reaction mixture was stirred at reflux overnight, then cooled to RT. MP-TsOH resin (4.07 mmol/g, 2 g) was added to the reaction mixture and the resulting mixture stirred for 1 hr. The resin was then filtered from the reaction mixture and thoroughly washed with MeOH. The isolated resin was then washed separately with ammonia (7 N in MeOH) and the filtrate was concentrated to an oil. The crude material was purified via column chromatography (5% EtOAc/hexanes) to give the desired product (0.26 g, 93.5% ee, 44% yield). 1H NMR (300 MHz, CDCl3) δ 3.73 (s, 2H), 4.22 (d, 1H), 5.12 (d, 1H), 5.22 (dd, 1H), 5.89-6.01 (m, 1H), 7.21-7.38 (m, 10H). MS APCI, m/z=224 (M+1). LC/MS 1.79 min., Method A.

Workup

  1. temperatureat reflux overnight
  2. stirringthe resulting mixture stirred for 1 hr
  3. filtrationThe resin was then filtered from the reaction mixture
  4. washthoroughly washed with MeOH
  5. washThe isolated resin was then washed separately with ammonia (7 N in MeOH)
  6. concentrationthe filtrate was concentrated to an oil
  7. customThe crude material was purified via column chromatography (5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-622ee2f952ba440ca03968ab37627691
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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