1,2-Dimethoxyethane → HCID 18723402, compound

HRID 1799517Notes

Reaction equation

HRID 1799517 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(COC)OC.CC(C)([O-])C.[Na+].Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=1>O>[F:37][C:36]([F:38])([F:39])[O:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 80711,2-Dimethoxyethane2×HCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 18723402HCID 18723402, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
9.5 °C

Procedure

10.00 kg of tert-butyl 4-hydroxypiperidin-1-carboxylate, 40 L of dimethoxyethane and 9.55 kg of sodium tert-butoxide were mixed, and stirred at 2 to 17° C. for 30 min. The mixture was mixed with 13.31 kg of 4-bromomethyl-1-trifluoromethoxybenzene and 10 L of dimethoxyethane at 12 to 14° C., and stirred at 21 to 23° C. for 3 hours. The reaction mixture was diluted with 100 L of water; extracted with 100 L of ethyl acetate; and the organic layer was washed with 100 L of a 1% NaCl aqueous solution twice. The organic layer was concentrated under reduced pressure to quantitatively obtain 19.21 kg of a yellow oily target substance.

Workup

  1. stirringstirred at 21 to 23° C. for 3 hours
  2. extractionextracted with 100 L of ethyl acetate
  3. washand the organic layer was washed with 100 L of a 1% NaCl aqueous solution twice
  4. concentrationThe organic layer was concentrated under reduced pressure to quantitatively obtain 19.21 kg of a yellow oily target substance

Sources & evidence

ORD record
ord-223df4abcc6f40439dd0d968a29247e2
Source dataset
uspto-grants-2013_01
Patent number
US08344148B2

Reaction notes

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