Lithium triethylborohydride → HCID 131734808, compound

HRID 1056932Notes

Reaction equation

HRID 1056932 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH2:11][C@H:12]4[C:18](=O)[N:17](COCC[Si](C)(C)C)[C:16]5[CH:28]=[C:29]([O:34][CH2:35][CH2:36][CH2:37][O:38][C:39]6[C:40]([O:96][CH3:97])=[CH:41][C:42]7[C:48](=[O:49])[N:47]8[CH:50]=[C:51]([C:53]#[C:54][CH2:55][NH:56][C:57](=[O:85])[C@@H:58]([NH:60][C:61](=[O:84])[C@@H:62]([NH:66][C:67](=[O:83])[O:68][CH2:69][CH:70]9[C:82]%10[CH:81]=[CH:80][CH:79]=[CH:78][C:77]=%10[C:76]%10[C:71]9=[CH:72][CH:73]=[CH:74][CH:75]=%10)[CH:63]([CH3:65])[CH3:64])[CH3:59])[CH2:52][C@H:46]8[C:45](=O)[N:44](COCC[Si](C)(C)C)[C:43]=7[CH:95]=6)[C:30]([O:32][CH3:33])=[CH:31][C:15]=5[C:14](=[O:98])[N:13]4[CH:99]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[Li+].[B-](CC)(CC)CC>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH2:11][C@H:12]4[CH:18]=[N:17][C:16]5[CH:28]=[C:29]([O:34][CH2:35][CH2:36][CH2:37][O:38][C:39]6[C:40]([O:96][CH3:97])=[CH:41][C:42]7[C:48](=[O:49])[N:47]8[CH:50]=[C:51]([C:53]#[C:54][CH2:55][NH:56][C:57](=[O:85])[C@@H:58]([NH:60][C:61](=[O:84])[C@H:62]([NH:66][C:67](=[O:83])[O:68][CH2:69][CH:70]9[C:71]%10[CH:72]=[CH:73][CH:74]=[CH:75][C:76]=%10[C:77]%10[C:82]9=[CH:81][CH:80]=[CH:79][CH:78]=%10)[CH:63]([CH3:64])[CH3:65])[CH3:59])[CH2:52][C@H:46]8[CH:45]=[N:44][C:43]=7[CH:95]=6)[C:30]([O:32][CH3:33])=[CH:31][C:15]=5[C:14](=[O:98])[N:13]4[CH:99]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 23712863Lithium triethylborohydrideHCID 131734809HCID 131734809, compound

Product 1

HCID 131734808HCID 131734808, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The SEM dilactam 10d (0.063 g, 0.0455 mmol, 1.0 eq.) was solubilised in THF (2.7) and cooled to −78° C. under a nitrogen atmosphere. Super hydride solution (1M in THF, 0.093 mL, 2.04 eq.) was added dropwise over 5 minutes. After 20 minutes an aliquot was washed with water for LCMS and TLC analysis. After 30 minutes water was added and the cold bath removed. The organic layer was extracted with EtOAc (2×10 mL) and the combined organic extracts washed with brine (10 mL), dried with MgSO4, filtered and the solvent removed under reduced pressure. The crude product was dissolved in MeOH/DCM/water (6:3:1) (0.01 M) and enough silica gel to form a thick stirring suspension.

Workup

  1. washAfter 20 minutes an aliquot was washed with water for LCMS and TLC analysis
  2. additionAfter 30 minutes water was added
  3. customthe cold bath removed
  4. extractionThe organic layer was extracted with EtOAc (2×10 mL)
  5. washthe combined organic extracts washed with brine (10 mL)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. dissolutionThe crude product was dissolved in MeOH/DCM/water (6:3:1) (0.01 M)
  10. customenough silica gel to form a thick stirring suspension

Sources & evidence

ORD record
ord-4c44603535c547528dd1e90c21391f63
Source dataset
uspto-grants-2016_07
Patent number
US09399641B2

Reaction notes

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