(S)-(-)-1-(2-Methoxybenzoyl)-2-pyrrolidinemethanol → Anthracene

HRID 1857664Notes

Reaction equation

HRID 1857664 reaction equation
CCCC[Si](CC)CC.[CH2:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:18]=[CH:19][C:20]1C=C[C:23](C=C)=[CH:22][CH:21]=1.[SiH4].COC1C=CC=CC=1C(N1CCC[C@H]1CO)=O>C(Cl)Cl>[CH:16]1[C:17]2[C:12](=[CH:11][C:10]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 643446(S)-(-)-1-(2-Methoxybenzoyl)-2-pyrrolidinemethanolHCID 131722152HCID 131722152, compound

Product 1

HCID 8418AnthraceneYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

We were able to successfully load representative primary alcohols to silane resin VIIIa and cleave the resins to afford high yields of alcohol products (Scheme 13). In a typical experiment, 200 mg PS-DES-silane resin was combined with a DCM solution of 1.7 mg of Rh2 (pfb)4 in 10 mL round bottle flask under argon. Then 66 mg of (s)-(-)-1-(2-methoxybenzoyl)-2-pyrrolidinemethanol was added at room temperature and the reaction was monitored by IR. After 3 hrs, the reaction was complete (as evidenced by the disappearance of the Si-H stretch at 2100 cm-1), the reaction mixture was filtered, and washed with 3×DCM, 2×toluene, 2×THF/H2O (1:1), 3×THF. The product was dried under vacuum in a dessicator. This product was then treated with AcOH/THF/H2O (6:6:1) for 12 hrs and the filtrate was concentrated by speedvac (rt, 80 mins) to obtain alcohol with 99.3% yield (GC, anthracene as internal standard).

Workup

  1. filtrationwas filtered
  2. washwashed with 3×DCM, 2×toluene, 2×THF/H2O (1:1), 3×THF
  3. customThe product was dried under vacuum in a dessicator
  4. additionThis product was then treated with AcOH/THF/H2O (6:6:1) for 12 hrs
  5. concentrationthe filtrate was concentrated by speedvac (rt, 80 mins)

Sources & evidence

ORD record
ord-fc099db1207849019913d5c474995b5a
Source dataset
uspto-grants-2000_11
Patent number
US06147159

Reaction notes

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