Benzyl Bromide → (3R,4R)-1-Benzyl-4-hydroxy-3-pyrrolidinemethanol

HRID 424728Notes

Reaction equation

HRID 424728 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][CH2:4][C@@H:3]1[CH2:7][OH:8].C(N(CC)CC)C.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH2:16]([N:5]1[CH2:6][C@H:2]([OH:1])[C@@H:3]([CH2:7][OH:8])[CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 10080382(3R,4R)-(4-Hydroxypyrrolidin-3-yl)methanol

Product 1

HCID 11579361(3R,4R)-1-Benzyl-4-hydroxy-3-pyrrolidinemethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3R,4R)-(4-Hydroxypyrrolidin-3-yl)methanol (1.18 g) was dissolved in ethanol (25 mL). To this solution, triethylamine (1.40 mL) was added and while the mixture was chilled in a salt/ice water bath, benzyl bromide (1.10 mL) was added dropwise. The mixture was stirred at room temperature for 1 hour and was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: ethyl acetate: methanol=20:1) to give (3R,4R)-(1-benzyl-4-hydroxypyrrolidin-3-yl)methanol as a milky white syrup (1.02 g).

Workup

  1. additionwas added dropwise
  2. concentrationwas concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (eluant: ethyl acetate: methanol=20:1)

Sources & evidence

ORD record
ord-45d604a9eb9446e59c97bf6fc8d6e826
Source dataset
uspto-grants-2012_01
Patent number
US08106072B2

Reaction notes

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