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

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.

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

ORDレコード

ord-0e4db0ca71b5492dbedda7241f09fec1

出典データセット

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07196104B2