Lithium tri-s-butylborohydride → HCID 178521623, compound

HRID 2047508Notes

Reaction equation

HRID 2047508 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]=[C:7]([CH:9]3[CH2:12][C:11](=[O:13])[CH2:10]3)[S:8][C:4]=2[CH:3]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1>[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]=[C:7]([C@@H:9]3[CH2:10][C@H:11]([OH:13])[CH2:12]3)[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 671459253-(6-Bromobenzothiazol-2-yl)cyclobutanone

Product 1

HCID 178521623HCID 178521623, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The product of Example 1C (710 mg, 2.52 mmole) was dissolved in 50 ml anhydrous THF and cooled to 0° C. L-selectride (1.0M in THF, 3.02 ml, 3.02 mmole) was added slowly. The mixture was stirred at 0° C. for 10 minutes, then warmed to room temperature for 30 minutes. It was then quenched with 1N sodium hydroxide (20 ml) and extracted three times with ethyl acetate. The organics were combined, dried over sodium sulfate and concentrated to give the crude product, which was used in the next step without further purification.

Workup

  1. temperaturewarmed to room temperature for 30 minutes
  2. customIt was then quenched with 1N sodium hydroxide (20 ml)
  3. extractionextracted three times with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-55ba0e4605a5451d9b92f8b6b6edfa57
Source dataset
uspto-grants-2013_11
Patent number
US08592467B2

Reaction notes

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