Sodium;3-oxidodioxaborirane;tetrahydrate → HCID 59837669, compound

HRID 273534Notes

Reaction equation

HRID 273534 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([S:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B1([O-])OO1.[OH2:29].[OH2:30].O.O.[Na+]>CC(O)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([S:17]([C:18]2[CH:19]=[CH:20][C:21]([Br:24])=[CH:22][CH:23]=2)(=[O:30])=[O:29])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 59837774HCID 59837774, compound

Product 1

HCID 59837669HCID 59837669, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-(4-bromo-phenylsulfanyl)-piperidine-1-carboxylic acid benzyl ester (1.2 g, 2.96 mmol, 1 equiv) and sodium perborate tetrahydrate (NaBO3.4H2O) (1.36 g, 8.87 mmol, 3 equiv) were heated to 55° C. in HOAc and stirred for 18 h. The reaction was cooled to room temperature and poured onto water. The aqueous phase was extracted with EtOAc (3×100 mL). The organic phases were combined and washed carefully with saturated sodium bicarbonate solution (CAUTION: copious gas evolution), dried over sodium sulfate, filtered and evaporated to yield a white solid (1.2 g, 93% yield). Rf=0.16 (20% EtOAc/hexanes).

Workup

  1. additionpoured onto water
  2. extractionThe aqueous phase was extracted with EtOAc (3×100 mL)
  3. washwashed carefully with saturated sodium bicarbonate solution (CAUTION: copious gas evolution)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e2aae917e40a4a50a7cfabbc1402bc8c
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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