Ethyl bromoacetate → HCID 59652041, compound

HRID 2042646Notes

Reaction equation

HRID 2042646 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[C:17]([F:24])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH2:22][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:17]([F:24])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 59651884HCID 59651884, compound

Product 1

HCID 59652041HCID 59652041, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 250 mL round bottom flask, 4-(4-acetyl-3-fluoro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (4.0 g, 12 mmol) in tetrahydrofuran (00 mL) were cooled to −78° C. Lithium diisopropylamide (1.4 g, 13 mmol) was added and stirred 30 min. then warmed to 0° C. Re-cooled to −78° C. and ethyl bromoacetate (1.4 mL, 13 mmol) in tetrahydrofuran (25 mL) was added. The reaction warmed to ambient temperature over 14 h. The reaction was quenched with NH4Cl sol. and the solvents were concentrated under vacuum. The reaction was chromatographed through silica gel with hexanes/ethyl acetate (7:3) as eluent to produce 4.10 g (82%) of oil.

Workup

  1. temperatureThe reaction warmed to ambient temperature over 14 h
  2. customThe reaction was quenched with NH4Cl sol.
  3. concentrationthe solvents were concentrated under vacuum
  4. customThe reaction was chromatographed through silica gel with hexanes/ethyl acetate (7:3) as eluent

Sources & evidence

ORD record
ord-499e6d1abcae4657b9002c89efb1466d
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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