HCID 21348552, compound → HCID 68491948, compound

HRID 2237358Notes

Reaction equation

HRID 2237358 reaction equation
[CH2:1]([C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>[Pd]>[C:5]1([CH2:6][CH2:7][CH2:8][CH2:3][CH:2]=[CH:1][C@@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH:4]=[CH:3][CH:2]=[CH:1][CH:9]=1

Participants

3

Reactant 1

HCID 21348552HCID 21348552, compound

Product 1

HCID 68491948HCID 68491948, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(S)-2-phenethyl-N-Boc-pyrrolidine (44 a) (PAA 2-28). A 10-mL round-bottom flask fitted with a 3-way tap and balloon was charged with 160 mg of 10% Pd—C. The flask was evacuated and filled with hydrogen gas 10 times. EtOH (5 mL) was added via syringe and stirred for several minutes. Alkene 45 a (260 mg,) in 2 mL EtOH was added via syringe and stirred for 24 h. Hydrogen gas was added as the balloon deflated. Upon complete reaction the catalyst was removed by filtration. The product was concentrated in vacuo to yield 251 mg (97%) of colorless oil. 1H NMR (CDCl3, 300 MHz) δ 7.19-7.30 (m, 5H), 3.76-3.88 (br m, 1H), 3.34-3.43 (br m, 2H), 2.59-2.62 (m, 2H), 1.62-2.16 (m, 6H), 1.46 (s, 9H).

Workup

  1. customA 10-mL round-bottom flask fitted with a 3-way tap and balloon
  2. customThe flask was evacuated
  3. additionfilled with hydrogen gas 10 times
  4. additionEtOH (5 mL) was added via syringe
  5. additionAlkene 45 a (260 mg,) in 2 mL EtOH was added via syringe
  6. stirringstirred for 24 h
  7. additionHydrogen gas was added as the balloon
  8. customUpon complete reaction the catalyst
  9. customwas removed by filtration
  10. concentrationThe product was concentrated in vacuo

Sources & evidence

ORD record
ord-52a56e793cf04ffaaf9aa1993c37dee4
Source dataset
uspto-grants-2010_05
Patent number
US07718600B2

Reaction notes

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