Lithium tri-s-butylborohydride → HCID 19100632, compound

HRID 1975060Notes

Reaction equation

HRID 1975060 reaction equation
[C:1]([N:20]1[N:24]=[N:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH:31]2[CH2:36][CH2:35][CH:34]([CH:37]=[O:38])[CH2:33][CH2:32]2)=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1>[C:1]([N:20]1[N:24]=[N:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH:31]2[CH2:36][CH2:35][CH:34]([CH2:37][OH:38])[CH2:33][CH2:32]2)=[N:21]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydride2×HCID 19100666HCID 19100666, compound

Product 1

HCID 19100632HCID 19100632, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

A 50 ml round-bottom flask, equipped with a magnetic stirring bar, septum, and nitrogen inlet, was charged with 220 mg (0.44 mmol, 1.0 equiv) of 1-[2-(2-trityl-tetrazol-5-yl)phenyl]-4-formylcyclohexane (from Step G) and 4 ml THF (over sieves). Into this clear solution, after being cooled down to -25° C., was added 530 μl (1.0M solution in THF, 0.53 mmol, 1.2 equiv) L-Selectride solution. After one hour, another 530 μl of L-Selectride solution was added to push the reaction to completion. The reaction was quenched after 1.5 hours with saturated aqueous sodium bicarbonate solution. Ethyl acetate was added to dissolve the organics. Layers were separated, and the aqueous layer was extracted with 5×10 ml ethyl acetate. The combined organic portion was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, concentrated, and chromatographed on a silica gel column (3 cm×31 cm, 4:6:1=hexane:methylene chloride:ethyl acetate, 1% distilled triethylamine) to afford 180 mg (82%) of the title alcohol: Rf=0.32 (4:6:1=hexane:methylene chloride:ethyl acetate, 1% distilled triethylamine); 1H NMR δ3.71-3.67 (dd, CHCH2OH from one isomer), 3.38-3.32 (dd, CHCH2OH from the other isomer), 3.10-3.00 (tt, CH2CHCH2); 13C NMR δ68.6, 40.2, 40.0, 33.2, 29.4.

Workup

  1. customA 50 ml round-bottom flask, equipped with a magnetic stirring bar
  2. customthe reaction to completion
  3. customThe reaction was quenched after 1.5 hours with saturated aqueous sodium bicarbonate solution
  4. additionEthyl acetate was added
  5. dissolutionto dissolve the organics
  6. customLayers were separated
  7. extractionthe aqueous layer was extracted with 5×10 ml ethyl acetate
  8. washThe combined organic portion was washed with saturated aqueous sodium bicarbonate solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. distillationchromatographed on a silica gel column (3 cm×31 cm, 4:6:1=hexane:methylene chloride:ethyl acetate, 1% distilled triethylamine)

Sources & evidence

ORD record
ord-6290df79f1bd48d6974149c83197ef89
Source dataset
uspto-grants-1994_02
Patent number
US05284841

Reaction notes

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