Methanol → Benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 440455

Reaction equation

HRID 440455 reaction equation
[C:1]([N:11]1[CH2:18][CH:17]([OH:19])[CH2:16][C@H:12]1[C:13](O)=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].B.CSC.CO>C1COCC1>[CH2:4]([O:3][C:1]([N:11]1[CH:12]([CH2:13][OH:14])[CH2:16][CH:17]([OH:19])[CH2:18]1)=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 12731799(2S)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 4283280Benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-CBz-4-hydroxy-L-proline (38.1 mmol) in 250 ml THF was added borane-methyl sulfide (78 mmol) dropwise at room temperature. After the evolution of H2 had ceased, the solution was heated to reflux with mechanical stirring. After 1 hour a white precipitate had formed. Methanol was carefully added, and the resulting solution refluxed for a further 15 minutes. The solution was cooled to room temperature, the solvents evaporated under reduced pressure, and the residual gum coevaporated with 2×100 ml MeOH. The product was obtained as a viscous oil in quantitative yield and identified by NMR.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux with mechanical stirring
  3. customAfter 1 hour a white precipitate had formed
  4. temperaturethe resulting solution refluxed for a further 15 minutes
  5. customthe solvents evaporated under reduced pressure
  6. customThe product was obtained as a viscous oil in quantitative yield

Sources & evidence

ORD record
ord-2ea1988bfba749139c8eae86dd09a893
Source dataset
uspto-grants-1996_05
Patent number
US05519134

Linked notes

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