Acetic Acid → 1-(4-Ethynylphenyl)pyrrolidine

HRID 447342

Reaktionsgleichung

Reaktionsgleichung von HRID 447342
C(O)(=O)C.[C:5]([C:7]1[CH:14]=[CH:13][C:10](C=O)=[CH:9][CH:8]=1)#[CH:6].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[C:5]([C:7]1[CH:8]=[CH:9][C:10]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:13][CH:14]=1)#[CH:6]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 27716454-EthynylbenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 858994401-(4-Ethynylphenyl)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Glacial acetic acid (0.2 mL) was added to a mixture of 4-ethynylbenzaldehyde (1 g, 7.5 mmol), pyrrolidine (1.2 mL, 15 mmol) and NaBH(OAc)3 (2.5 g, 11.5 mmol) in DCE (35 mL). The resulting mixture was stirred for 2 h at rt. The reaction was quenched with saturated aqueous NaHCO3 (50 mL). The product was extracted into CH2Cl2 (2×100 mL), and the combined organic layer was washed with brine (25 mL), dried (MgSO4) and evaporated in vacuo to give 1-(4-ethynylphenyl)pyrrolidine in quantitative yield. 1H NMR (CDCl3) δ: 7.45 (d, J=7.8 Hz, 2H), 7.30 (d, J=8.3 Hz, 2H), 3.62 (s, 2H), 3.06 (s, 1H), 2.51 (bs, 4H), 1.80 (bs, 4H).

Aufarbeitung

  1. customThe reaction was quenched with saturated aqueous NaHCO3 (50 mL)
  2. extractionThe product was extracted into CH2Cl2 (2×100 mL)
  3. washthe combined organic layer was washed with brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-08a2c9f9aa2b4ba6b7c79cfc6b501fb0
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481533B2

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