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

HRID 460214

Reaction equation

HRID 460214 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

HCID 187719784-(Pyrrolidin-1-ylmethyl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0e4db0ca71b5492dbedda7241f09fec1
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Linked notes

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