2,5-Dichloropyridine → HCID 71547980, compound

HRID 1184563Notes

Reaction equation

HRID 1184563 reaction equation
[OH:1][C@H:2]1[CH2:17][N:5]2[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C@@H:4]2[CH2:3]1.Cl[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=1.CC(C)([O-])C.[K+]>O1CCCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([O:1][C@H:2]2[CH2:17][N:5]3[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:9][C@@H:4]3[CH2:3]2)=[N:20][CH:21]=1

Participants

5

Reactant 3

HCID 276852,5-DichloropyridineHCID 23665647Potassium tert-butoxideHCID 71305241HCID 71305241, compound

Product 1

HCID 71547980HCID 71547980, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (7R,8aS)-tert-butyl 7-hydroxyhexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (485 mg, 2 mmol) and 2,5-dichloropyridine (326 mg, 2.2 mmol) in tetrahydrofuran (4 mL) was added potassium tert-butoxide (3 mL, 1 M in tetrahydrofuran). The mixture was stirred at room temperature overnight. The reaction was quenched with water (10 mL), and the crude product was extracted with dichloromethane (2×50 mL). The combined organic fractions were concentrated, and the residue was purified by chromatography on silica gel (dichloromethane/methanol=15:1) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40 (s, 9H), 1.80 (m, 2H), 2.06-2.16 (m, 3H), 2.53 (m, 1H), 2.75-2.90 (m, 2H), 3.60 (m, 1H), 3.90-4.10 (m, 2H), 5.25 (m, 1H), 6.83 (d, 1H, J=7 Hz), 7.80 (d, 1H, J=7 Hz), 8.20 (s, 1H); MS (ESI) m/z 354 (M+H)+.

Workup

  1. customThe reaction was quenched with water (10 mL)
  2. extractionthe crude product was extracted with dichloromethane (2×50 mL)
  3. concentrationThe combined organic fractions were concentrated
  4. customthe residue was purified by chromatography on silica gel (dichloromethane/methanol=15:1)

Sources & evidence

ORD record
ord-92b69003b5c8406d8dbd511bb083aa69
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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