Water → HCID 40209778, compound

HRID 1160209Notes

Reaction equation

HRID 1160209 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:18]([N:25]1[CH2:29][CH2:28][C@H:27]([NH2:30])[CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CCOCC>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:30][C@H:27]2[CH2:28][CH2:29][N:25]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 743734-Iodobenzoyl chlorideHCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidine

Product 1

HCID 40209778HCID 40209778, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4-iodobenzoyl chloride (10 g, 37 mmol) in ether (400 mL) at 0° C. was added triethylamine (4.7 g, 45 mmol). (3-S)-1-Benzyl-3-aminopyrrolidine (7.3 g, 41 mmol) in ether (100 mL) was then added slowly via dropping funnel at 0° C. After the addition was complete, the mixture was further stirred for 18 hrs. Water (200 mL) was added and the mixture extracted with methylene chloride (3×200 mL) dried and concentrated to give the title compound (9.7 g, 64%) as beige powder. 1H NMR (CDCl3) δ: 7.79 (m, 2H), 7.47 (m, 2H), 7.26-7.35 (m, 5H), 6.51 (d, 1H, J=8.8 Hz), 4.62-4.68 (m, 1H), 3.63 (s, 2H), 2.91-2.96 (m, 1H), 2.70-2.74 (m, 1H), 2.58-2.63 (m, 1H), 2.25-2.44 (m, 2H), 1.68-1.77 (m, 1H).

Workup

  1. customat 0° C
  2. additionAfter the addition
  3. extractionthe mixture extracted with methylene chloride (3×200 mL)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2ddf5a0e73d44535aa5d45b061c73001
Source dataset
uspto-grants-2010_10
Patent number
US07816354B2

Reaction notes

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