Methanol → HCID 83853109, compound

HRID 1475315Notes

Reaction equation

HRID 1475315 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH2:15][CH2:14][CH2:13][CH2:12]3)[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]3([CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 22763132HCID 22763132, compound

Product 1

HCID 83853109HCID 83853109, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of borane-dimethyl sulfide complex in THF (2 M, 3.75 mL) was added to 6′ chloro-spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one under nitrogen and the resulting solution stirred at 20° C. for 0.2 h then at reflux for 1 h. The mixture was cooled then MeOH (3 mL) was added slowly (caution,) and reflux resumed for 1 h. Excess solvent was evaporated in vacuo and chromatography of the residue (SiO2; gradient elution with 0-40% Et2O in petrol) gave the title compound (0.335 g, 88%). MS: [M+H]+=208.

Workup

  1. temperatureat reflux for 1 h
  2. temperatureThe mixture was cooled
  3. temperaturereflux
  4. waitresumed for 1 h
  5. customExcess solvent was evaporated in vacuo and chromatography of the residue (SiO2; gradient elution with 0-40% Et2O in petrol)

Sources & evidence

ORD record
ord-5588bf51665342b5857fa58ba9fd0d3c
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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