Methanol → HCID 70981654, compound

HRID 1475341Notes

Reaction equation

HRID 1475341 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:14][OH:15])([CH2:12][OH:13])[C:7](=O)[NH:8]2)=[CH:4][CH:3]=1.CO>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:12][OH:13])([CH2:14][OH:15])[CH2:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 70981368HCID 70981368, compound

Product 1

HCID 70981654HCID 70981654, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

A mixture of 6-chloro-3,3-bis-hydroxymethyl-1,3-dihydro-indol-2-one (5.8 mmol), THF (10 mL) and a solution of borane-dimethylsulfide complex in THF (2 M, 30 mL) was heated at 70° C. for 3 h, then cooled to 20° C. MeOH (30 mL) was added dropwise (caution,) over 0.2 h, then mixture was heated at reflux for 2 h. Resulting mixture was cooled then evaporated in vacuo to give an oily residue. Chromatography (SiO2; gradient elution with 20-100% EtOAc in petrol) gave the title compound (1.15 g) as an oil which crystallised. MS: [M+H]+=214.

Workup

  1. temperaturemixture was heated
  2. temperatureat reflux for 2 h
  3. customResulting mixture
  4. temperaturewas cooled
  5. customthen evaporated in vacuo
  6. customto give an oily residue
  7. washChromatography (SiO2; gradient elution with 20-100% EtOAc in petrol)

Sources & evidence

ORD record
ord-703306192f51478fb415b62c544fc839
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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