Acetic Acid → HCID 86713712, compound

HRID 718005Notes

Reaction equation

HRID 718005 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH:10]([CH:14]=O)[CH2:9]2)=[CH:4][CH:3]=1.[NH2:16][CH2:17][CH2:18][OH:19].C(O)(=O)C.[BH4-].[Na+]>CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:16][CH2:17][CH2:18][OH:19])[CH2:9]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 700EthanolamineHCID 4311764Sodium borohydrideHCID 86713711HCID 86713711, compound

Product 1

HCID 86713712HCID 86713712, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of C6 (338 mg, 1.52 mmol) in methanol (5 mL) was added 2-aminoethanol (139 mg, 2.28 mmol) followed by acetic acid (89 μL, 1.55 mmol). The reaction was stirred at reflux for 2 hours, then cooled to 0° C. Sodium borohydride (115 mg, 3.04 mmol) was added and the mixture was allowed to warm to room temperature. The reaction was diluted with ethyl acetate, quenched with water, and then extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to provide the crude title compound as a liquid. Yield: 362 mg, 1.35 mmol, 89%. This was presumed to be a mixture of stereoisomers. LCMS m/z 268.3 (M+1). 1H NMR (400 MHz, CDCl3), characteristic peaks: δ 7.22-7.28 (m, 2H), 7.10-7.16 (m, 2H), 3.63 (dd, J=5.3, 5.1 Hz, 2H), 2.75 (dd, J=5.3, 5.1 Hz, 2H).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureto warm to room temperature
  3. customquenched with water
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-105e2ca12c2c4946b79640dae2a77cbf
Source dataset
uspto-grants-2015_11
Patent number
US09193726B2

Reaction notes

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