Acetic Acid → HCID 70874896, compound

HRID 2208930Notes

Reaction equation

HRID 2208930 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[O:14]1[C:18]2([CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]2)[O:17][CH2:16][CH2:15]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[O:14]1[C:18]2([CH2:23][CH2:22][CH:21]([NH:1][C:2]3[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=3)[C:5]([O:7][CH3:8])=[O:6])[CH2:20][CH2:19]2)[O:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydrideHCID 68295455Methyl 3-amino-5-chloro-2-methylbenzoate

Product 1

HCID 70874896HCID 70874896, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate (5.0 g, 25 mmol) and 1,4-dioxaspiro[4.5]decan-8-one (5.86 g, 37.8 mmol) in dichloroethane (50 mL) was added acetic acid (9.0 g, 150 mmol) and the reaction mixture stirred at room temperature for 10 minutes. Then sodium triacetoxyborohydride (15.9 g, 752 mmol) was added at 0° C. and the reaction stirred overnight at room temperature. On completion, the reaction was quenched with aqueous sodium bicarbonate, the organic phase separated and the aqueous phase extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography to afford the title compound (6.6 g, 76%).

Workup

  1. stirringthe reaction stirred overnight at room temperature
  2. customOn completion, the reaction was quenched with aqueous sodium bicarbonate
  3. customthe organic phase separated
  4. extractionthe aqueous phase extracted with dichloromethane
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-17f175b9fe7b4239a803819b08a7a68b
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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