Borane;tetrahydrofuran → Methyl 2-(3-(3-(diphenyl(2-methyl-2-propyl)siloxy)phenyl)-3-(R)-hydroxy-propyl)benzoate

HRID 258481Notes

Reaction equation

HRID 258481 reaction equation
CB1N2CCC[C@H]2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.[C:22]1([Si:28]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)([C:50]([CH3:53])([CH3:52])[CH3:51])[O:29][C:30]2[CH:31]=[C:32]([C:36](=[O:49])[CH2:37][CH2:38][C:39]3[CH:48]=[CH:47][CH:46]=[CH:45][C:40]=3[C:41]([O:43][CH3:44])=[O:42])[CH:33]=[CH:34][CH:35]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.B.C1COCC1>C1COCC1>[C:54]1([Si:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:50]([CH3:51])([CH3:52])[CH3:53])[O:29][C:30]2[CH:31]=[C:32]([C@H:36]([OH:49])[CH2:37][CH2:38][C:39]3[CH:48]=[CH:47][CH:46]=[CH:45][C:40]=3[C:41]([O:43][CH3:44])=[O:42])[CH:33]=[CH:34][CH:35]=2)[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Participants

5

Reactant 3

HCID 2723981Borane;tetrahydrofuranHCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 23173847Methyl 2-(3-(3-(diphenyl(2-methyl-2-propyl)siloxy)phenyl)-3-oxopropyl)benzoate

Product 1

HCID 22848862Methyl 2-(3-(3-(diphenyl(2-methyl-2-propyl)siloxy)phenyl)-3-(R)-hydroxy-propyl)benzoateYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At -20° C., (S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo(1,2-c)(1,3,2)oxazaborole (J. Am. Chem. Soc., 104, 5551-5553 (1987), 3.82 g, 0.014 mol) was added to a solution of the ketone of Step 2 in THF (556 mL). To this mixture, 1.0M BH3.THF (111 mL) was slowly added within 10 min. After 15 min, the reaction was quenched with 2M HCl (250 mL). After extraction with EtOAc, the organic phase was washed with 25% aq NH4OAc followed by saturated NaCl. The solvent was removed at reduced pressure to afford an oil which was purified by flash chromatography (20% EtOAc in hexane) to give 70 g (95%) of the title compound.

Workup

  1. customthe reaction was quenched with 2M HCl (250 mL)
  2. extractionAfter extraction with EtOAc
  3. washthe organic phase was washed with 25% aq NH4OAc
  4. customThe solvent was removed at reduced pressure
  5. customto afford an oil which
  6. customwas purified by flash chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-5b569cbf989e497e942bd5013a0a507e
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

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