99735-43-0 → (4R)-4-(Hydroxymethyl)-1-[(1R)-1-phenylethyl]pyrrolidin-2-one

HRID 1496848Notes

Reaction equation

HRID 1496848 reaction equation
[CH3:1][C@@H:2]([N:9]1[C:13](=[O:14])[CH2:12][C@@H:11]([C:15](O)=[O:16])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CSC.B>O1CCCC1>[OH:16][CH2:15][C@H:11]1[CH2:10][N:9]([C@@H:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH3:1])[C:13](=[O:14])[CH2:12]1

Participants

4

Reactant 2

HCID 72363499735-43-0HCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 13422564(4R)-4-(Hydroxymethyl)-1-[(1R)-1-phenylethyl]pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5 g (1′R,3R)-1-(1′Phenylethyl)-5-oxo-3-pyrrolidine carboxylic acid was dissolved in 50 mL tetrahydrofuran, then the solution was cooled to 0° C. 16.5 mL borane dimethyl sulfide (2 M in tetrahydrofuran) was added dropwise over 30 min and the reaction solution was slowly warmed to 25° C. and stirred for a further 2 h at 25° C. The reaction mixture was concentrated, diluted in dichloromethane and washed with sodium bicarbonate solution. The water phase was extracted with dichloromethane (×2) and the combined organic phases were dried over magnesium sulfate and concentrated.

Workup

  1. temperaturethe reaction solution was slowly warmed to 25° C.
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted in dichloromethane
  4. washwashed with sodium bicarbonate solution
  5. extractionThe water phase was extracted with dichloromethane (×2)
  6. dry with materialthe combined organic phases were dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-64660c9f03b142c4a4ad011d18310a1d
Source dataset
uspto-grants-2015_12
Patent number
US09199937B2

Reaction notes

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