Nitrogen → 4-(Benzyloxy)-1-(pyrrolidin-1-yl)butan-1-one

HRID 714225

Reaction equation

HRID 714225 reaction equation
N#N.[CH2:3]([O:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[CH2:3]([O:10][CH2:11][CH2:12][CH2:13][C:14]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

9

Reactant 6

HCID 947NitrogenHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5622014-(Benzyloxy)butanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 493711804-(Benzyloxy)-1-(pyrrolidin-1-yl)butan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-benzyloxybutyric acid (246 mg, 1.27 mmol), pyrrolidine (0.13 mL, 1.52 mmol), EDC.HCl (493 mg, 2.53 mmol), HOBt (262 mg, 1.90 mL) and DIPEA (0.65 mL, 3.80 mmol) in CH2Cl2 (10 mL) was heated at rt until completion of the reaction. Water was added, the layers separated and the aq. layer extracted with CH2Cl2 (2×). The combined org. extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 1:0→0:1) to give 4-(benzyloxy)-1-(pyrrolidin-1-yl)butan-1-one as a colorless oil. LC-MS-conditions 08: tR=0.77 min; [M+H]+=247.95.

Workup

  1. customthe layers separated
  2. extractionthe aq. layer extracted with CH2Cl2 (2×)
  3. washextracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by FC (hept-EA, 1:0→0:1)

Sources & evidence

ORD record
ord-e41d7a5469574e83ac8fe401c5c1d186
Source dataset
uspto-grants-2015_11
Patent number
US09187435B2

Linked notes

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