4-Hydroxybenzaldehyde → 4-(Pyrrolidin-1-ylmethyl)phenol

HRID 460214

Reaktionsgleichung

Reaktionsgleichung von HRID 460214
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:10]1([CH2:6][C:5]2[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

7

Edukt 5

HCID 1264-HydroxybenzaldehydeHCID 176Acetic AcidHCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 187719784-(Pyrrolidin-1-ylmethyl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-hydroxylbenzaldehyde (10 g, 81.9 mmol) in anhydrous CH2Cl2 (500 mL) at RT, under N2, pyrrolidine (10.2 mL, 122.9 mmol) was added, followed by NaBH(OAc)3 (34.6 g, 163.9 mmol) and AcOH (19.7 g, 327.8 mmol). After the mixture was stirred at RT for 24 h, a saturated solution of NaHCO3(aq) (150 mL) was added. The mixture was vigorously stirred for an additional 1 h and then extracted with CH2Cl2 (3×200 mL). The combined organic layer was washed with brine (300 mL), dried over MgSO4, filtered and concentrated under reduced pressure to yield the title compound as amber oil. This was used crude in the next step. MS m/z: 178 (M+1). Calc'd for C11H15NO-177.2.

Aufarbeitung

  1. stirringThe mixture was vigorously stirred for an additional 1 h
  2. extractionextracted with CH2Cl2 (3×200 mL)
  3. washThe combined organic layer was washed with brine (300 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0e4db0ca71b5492dbedda7241f09fec1
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196104B2

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