Water → 5-(Hydroxymethyl)indolizin-8-yl trifluoromethanesulfonate

HRID 1037066Notes

Reaction equation

HRID 1037066 reaction equation
[F:1][C:2]([F:22])([F:21])[S:3]([O:6][C:7]1[C:15]2[N:11]([CH:12]=[CH:13][CH:14]=2)[C:10]([C:16](OCC)=[O:17])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[BH4-].[Na+].O>CO>[F:22][C:2]([F:1])([F:21])[S:3]([O:6][C:7]1[C:15]2[N:11]([CH:12]=[CH:13][CH:14]=2)[C:10]([CH2:16][OH:17])=[CH:9][CH:8]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86685512Ethyl 8-(((trifluoromethyl)sulfonyl)oxy)indolizine-5-carboxylate

Product 1

HCID 866855115-(Hydroxymethyl)indolizin-8-yl trifluoromethanesulfonateYield 190.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 8-(((trifluoromethyl)sulfonyl)oxy)indolizine-5-carboxylate (30 g, 89 mmol) in MeOH (300 mL) was added NaBH4 (13.5 g, 0.356 mol) at 0° C. under N2. The reaction mixture was stirred at rt overnight. After the completion, to the reaction was added water, extracted with EtOAc, washed with brine, dried and concentrated to give the desired product 5-(hydroxymethyl)indolizin-8-yl trifluoromethanesulfonate (50 g, crude).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-27b9d756532b4dba9f5828f137753c32
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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