Lithium tri-s-butylborohydride → HCID 178521623, compound

HRID 2103662Notes

Reaction equation

HRID 2103662 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 1 N 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 1 N 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-06ddc816b97249c5b74a8511cb50ea3e
Source dataset
uspto-grants-2009_08
Patent number
US07576110B2

Reaction notes

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