Borane → HCID 178419238, compound

HRID 2082449Notes

Reaction equation

HRID 2082449 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.CSC.[BH3:23].B>C1(C)C=CC=CC=1>[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:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[BH3:23]

Participants

5

Reactant 3

HCID 6331BoraneHCID 27248992-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (S)-HCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 178419238HCID 178419238, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

A 250-mL three-necked flask fitted with a mechanical stirrer, nitrogen inlet tube, and teflon coated thermocouple probe, was charged with a solution of the free base product of Example 1 Step B (20.7 g, 81.7 mmol) in dry toluene (100 mL). To the stirred solution at 20° C. was added borane-dimethyl sulfide (10M, 10.0 mL, 100 mmol) over 5 minutes via syringe. The borane reacted immediately in an exothermic reaction (raising the internal temperature from 20° C. to 32° C.) forming a thick white precipitate. With continued stirring, the mixture was allowed to cool to room temperature (20° C.) over a 1 hour period. The mixture was filtered, and the product cake washed with dry toluene (25 mL). The product was dried in vacuo (20° C., 0.01 mBar) to constant weight. Yield 15.7 g (72%) of a white crystal line solid. m.p. 130°-132° C. (dec). 1H NMR (CDCl3 ) δ7.7-7.1 (m, 10H, Ar-H), 5.15 (s, 1H, --OH), 4.5 (br, 1H, --NH), 4.2 (m, 1H, C2-H), 3.25 (m, 2H, C5-H2), 2.6 (m, 1H, C4-H), 2.3 (m, 1H, C4-H), 1.85 (m, 1H, C3-H), 1.6 (m, 1H, C3-H), 2.1-0.7 (br, 3H, BH3). 13C NMR (CDCl3) δ145.8, 144.5 (C1', C1"), 129.1, 128.2 (C3', C5', C3", C5"), 127.4, 127.0 (C4', C4"), 125.2, 125.1 (C2', C6', C2", C6"), 76.5 (Cα), 69.6 (C2), 55.6 (C5), 20.6 (C4), 19.9 (C3).

Workup

  1. customA 250-mL three-necked flask fitted with a mechanical stirrer, nitrogen inlet tube
  2. temperatureraising the internal temperature from 20° C. to 32° C.)
  3. customforming a thick white precipitate
  4. filtrationThe mixture was filtered
  5. washthe product cake washed with dry toluene (25 mL)
  6. customThe product was dried in vacuo (20° C., 0.01 mBar) to constant weight

Sources & evidence

ORD record
ord-ee2cd53697cd4899a362dd37f21d6bbe
Source dataset
uspto-grants-1993_02
Patent number
US05189177

Reaction notes

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