Ammonium Chloride → HCID 71014250, compound

HRID 1430075Notes

Reaction equation

HRID 1430075 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.C([Li])CCC.[O:14]=[C:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.[Cl-].[NH4+]>C(Cl)Cl>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:15]2([OH:14])[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:19][CH2:20]2)[CH:7]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 27628362-Bromo-4-chloropyridineHCID 178418339Butyllithium

Product 1

HCID 71014250HCID 71014250, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 2-bromo-4-chloropyridine (C2) (1.00 g, 5.20 mmol) in CH2Cl2 (10 mL) cooled to −78° C. was added n-butyllithium (1.6 M in hexanes, 3.57 mL, 5.72 mmol) dropwise. After 15 min, a solution of tert-butyl 4-oxopiperidine-1-carboxylate (C1) (1.14 g, 5.72 mmol) in CH2Cl2 (3 mL) was added dropwise. After 1 h, saturated aqueous ammonium chloride (5 mL) was added. The mixture was warmed to ambient temperature, diluted with CH2Cl2 and washed with saturated aqueous sodium bicarbonate and brine. The organic solution was dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was purified via silica gel chromatography eluting with 0-20% ethyl acetate in hexanes to provide tert-butyl 4-(4-chloropyridin-2-yl)-4-hydroxypiperidine-1-carboxylate (C3).

Workup

  1. waitAfter 1 h
  2. washwashed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialThe organic solution was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified via silica gel chromatography
  7. washeluting with 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-024d63e80a3547c68fb4573b000c6d4e
Source dataset
uspto-grants-2015_01
Patent number
US08940765B2

Reaction notes

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