Acetic Acid → HCID 86677812, compound

HRID 1499888Notes

Reaction equation

HRID 1499888 reaction equation
[C:1]([C:4]1[C:5]([O:23][CH3:24])=[C:6]([CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)[C:7]([Cl:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>CO>[Cl:11][C:7]1[C:8]([Cl:10])=[CH:9][C:4]([CH:1]([OH:3])[CH3:2])=[C:5]([O:23][CH3:24])[C:6]=1[CH:12]1[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86666945HCID 86666945, compound

Product 1

HCID 86677812HCID 86677812, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 3-(3-acetyl-5,6-dichloro-2-methoxyphenyl)azetidine-1-carboxylate (9.6 g, 26 mmol) in methanol (240 mL) at 0° C. was treated with sodium tetrahydroborate (1.9 g, 51 mmol) portionwise over 5 min and stirred at 0° C. for 30 min. The reaction mixture was quenched with acetic acid (7.3 mL, 130 mmol) at 0° C. and treated with saturated sodium bicarbonate solution (˜50 mL). The reaction mixture was concentrated to remove most of the methanol (to ˜60 mL), poured into saturated sodium bicarbonate solution (150 ml), and extracted with ethyl acetate (2×200 mL). The combined organic extracts were washed with water and brine, dried over sodium sulfate, filtered, and concentrated to give the desired product (9.6 g, quantitative) that was used without further purification. LCMS for C13H16Cl2NO4 ([M-(t-Bu)+]+H)+: m/z=320.0; Found: 320.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove most of the methanol (to ˜60 mL)
  3. additionpoured into saturated sodium bicarbonate solution (150 ml)
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5370826a5b164c948944a965d9029032
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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