Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)borane → HCID 11063606, compound

HRID 1741826Notes

Reaction equation

HRID 1741826 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:15])[CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].B(Cl)([C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1)[C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1>O1CCCC1>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C@H:11]([OH:15])[CH2:12][CH2:13][CH3:14])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 9923113Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)boraneHCID 11183323HCID 11183323, compound

Product 1

HCID 11063606HCID 11063606, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4'-Isobutylbutanophenone (1.2 g) was added to a solution of (+)-B-chlorodiisopinocampheylborane (2.10 g) in tetrahydrofuran (4 ml) at 25° C. After 5 hours, the solvent was removed and the residue was dissolved in ethyl ether (20 ml). Diethanolamine (1.4 ml) was added to the mixture and the mixture was stirred for 2 hours. The solid was filtered off and washed with ethyl ether. The combined filtrates were concentrated and the residue was chromatographed on silica gel (eluent:hexane:CH2Cl2 =1:2) to give (R)-1-(4-isobutylphenyl)butan-1-ol (937 mg).

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl ether (20 ml)
  3. additionDiethanolamine (1.4 ml) was added to the mixture
  4. filtrationThe solid was filtered off
  5. washwashed with ethyl ether
  6. concentrationThe combined filtrates were concentrated
  7. customthe residue was chromatographed on silica gel (eluent:hexane:CH2Cl2 =1:2)

Sources & evidence

ORD record
ord-36683de1528746259013167460d8cef7
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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