Pyridine → HCID 86730034, compound

HRID 2199464Notes

Reaction equation

HRID 2199464 reaction equation
[NH2:1][C@:2]1([CH2:14][OH:15])[CH2:6][CH2:5][C@H:4]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[CH2:3]1.N1C=CC=CC=1.[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23]>O1CCOCC1.C(OCC)(=O)C>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C@H:4]2[CH2:5][CH2:6][C@@:2]3([NH:1][C:22](=[O:23])[O:15][CH2:14]3)[CH2:3]2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 682631,1'-CarbonyldiimidazoleHCID 67360553HCID 67360553, compound

Product 1

HCID 86730034HCID 86730034, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of ((1R,3S)-1-amino-3-(4-bromophenyl)cyclopentyl)methanol (11 g, 40.7 mmol) and pyridine (I-3A, 3.29 mL, 40.7 mmol) in dioxane (300 mL) was added 1,1′-carbonyldiimidazole (19.81 g, 122 mmol). The reaction mixture was stirred for 4 hours. The reaction mixture was diluted with ethyl acetate and washed with 1M HCl, brine and saturated NaHCO3. The mixture was back extracted several times. The organic layer was dried with MgSO4, filtered and concentrated to afford 10.5 g of desired product as an off-white solid. HPLC retention time=0.87 min (Condition G). LC/MS M+1=297.9; 1H NMR (400 MHz, chloroform-d) δ 7.45 (d, J=8.6 Hz, 2H), 7.12 (d, J=8.4 Hz, 2H), 6.42 (br. s., 1H), 4.41-4.21 (m, 2H), 3.17-2.91 (m, 1H), 2.34 (dd, J=13.3, 7.4 Hz, 1H), 2.23-2.11 (m, 2H), 2.01-1.90 (m, 2H), 1.88-1.74 (m, 1H).

Workup

  1. washwashed with 1M HCl, brine and saturated NaHCO3
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b0b34bc4606f4e88b38c15a263d3f026
Source dataset
uspto-grants-2016_06
Patent number
US09359286B2

Reaction notes

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