1,2-Dichloroethane → HCID 86669840, compound

HRID 564392Notes

Reaction equation

HRID 564392 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:19][CH2:18][C@@H:17]([NH2:20])[CH2:16]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C:21]([O:25][C:26]([NH:28][CH2:29][C:30](O)=[O:31])=[O:27])([CH3:24])([CH3:23])[CH3:22].C(Cl)CCl.O>N1C=CC=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:19][CH2:18][C@@H:17]([NH:20][C:30](=[O:31])[CH2:29][NH:28][C:26](=[O:27])[O:25][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:16]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 78288N-(tert-butoxycarbonyl)glycineHCID 67005110HCID 67005110, compound

Product 1

HCID 86669840HCID 86669840, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3R)-1-[1-(4-methoxyphenyl)piperidin-4-yl]pyrrolidin-3-amine (HCl salt, 1.2 g, 3.13 mmol), [(tert-butoxycarbonyl)amino]acetic acid (727 mg, 4.15 mmol) in 40 mL pyridine was added EDC (1.06 g, 5.5 mmol). After 16 hours at room temperature, water (10 mL) and CH2Cl2 (10 mL) were added and the organic layer was washed with brine, dried over Mg2SO4, filtered and concentrated. The crude mixture was subjected to flash chromatography to afford tert-butyl [2-({(3R)-1-[1-(4-methoxyphenyl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]carbamate (812 mg, 62%). To a solution of tert-butyl [2-({(3R)-1-[1-(4-methoxyphenyl)piperidinyl)pyrrolidin-3-yl}amino)-2-oxoethyl]carbamate (1.00 g, 2.31 mmol) in CH2Cl2 (10 mL) was added 4N HCl/dioxane (10 mL). After 2 hours, ether was added and 2-amino-N-{(3R)-1-[1-(4-methoxyphenyl)piperidin-4-yl]pyrrolidin-3-yl}acetamide (1.02 g, quant.)

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over Mg2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6c57431a06284cb4883b800c90b0c704
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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