Borane;tetrahydrofuran → HCID 101641816, compound

HRID 2166177Notes

Reaction equation

HRID 2166177 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C@@H:9]2[CH2:13][CH2:12][CH2:11][NH:10]2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH3:20].C1COCC1>>[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:8][BH:20][N:10]3[CH2:11][CH2:12][CH2:13][C@@H:9]23)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 27248992-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (S)-

Product 1

HCID 101641816HCID 101641816, compoundYield 25.4%

Procedure

(S)-(-)-α,α-diphenyl-2-pyrrolidinemethanol (378.5 mg, 1.5 mmol) was dissolved in 4.09 mL (4.5 mmol) of BH3.THF (1.1M), and the resulting solution was refluxed for 48 h under argon atmosphere (1 bar). The solvent was removed under vacuum, and the residue was sublimed (150°-160° C./0.1 Torr) to give 258 mg of a crude product. This product (94.1 mg) was resublimed (145°-160° C./0.05 Torr) to give 36.7 mg (0.139 mmol), 25.4% yield) of (S)-5,5-diphenyl-3,4-propano-1,3,2-oxazaborolidine as colorless crystals, mp 107°-124° C.,

Workup

  1. temperaturethe resulting solution was refluxed for 48 h under argon atmosphere (1 bar)
  2. customThe solvent was removed under vacuum
  3. custom(150°-160° C./0.1 Torr)
  4. customto give 258 mg of a crude product
  5. custom(145°-160° C./0.05 Torr)

Sources & evidence

ORD record
ord-23f993fb41ab4d5495f02d519478d993
Source dataset
uspto-grants-1990_07
Patent number
US04943635

Reaction notes

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