Formic Acid → Acetic Acid

HRID 1511870Notes

Reaction equation

HRID 1511870 reaction equation
[NH2:1][C@:2]1([CH2:24][OH:25])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:9][CH:8]=2)[CH2:3]1.[CH:26]([OH:28])=[O:27]>>[NH2:1][C@:2]1([CH2:24][OH:25])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:9][CH:8]=2)[CH2:3]1.[C:26]([OH:28])(=[O:27])[CH3:2]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 57554668HCID 57554668, compound

Product 2

HCID 176Acetic AcidYield 28.8%HCID 57554850HCID 57554850, compound

Conditions

Temperature
80 °C

Procedure

((1R,3R)-1-amino-3-(4-(5-phenylpent-1-ynyl)phenyl)cyclopentyl)methanol (900 mg, 2.70 mmol) was dissolved in formic acid (20 mL) and heated to about 80° C. After 4 h the reaction mixture was cooled to room temperature, concentrated in vacuo, diluted with water (10 mL) and reheated to about 80° C. After 4 h the reaction mixture was purified by RP HPLC. Concentration of the fractions containing the desired product provided 1-(4-((1R,3R)-3-amino-3-(hydroxymethyl)cyclopentyl)phenyl)-5-phenylpentan-1-one, Acetic Acid (320 mg, 0.778 mmol, 28.8% yield) as an off white foam.

Workup

  1. temperatureAfter 4 h the reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additiondiluted with water (10 mL)
  4. customreheated to about 80° C
  5. customAfter 4 h the reaction mixture was purified by RP HPLC
  6. additionConcentration of the fractions containing the desired product

Sources & evidence

ORD record
ord-c801462fc41642168c8611cc959084fc
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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