Benzyloxycarbonyl-L-proline → Cbz-L-Prolinol

HRID 1419844Notes

Reaction equation

HRID 1419844 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.CSC>O1CCCC1.C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 101987Benzyloxycarbonyl-L-prolineHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 11096562Cbz-L-ProlinolYield 81.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1(benzyloxycarbonyl)-L-proline (15 g) in tetrahydrofuran (150 ml) at 0° C., borane-methylsulfide complex (9 ml, 95% in dimethyl sulfide) was added and the reaction mixture was stirred at room temperature for 8 h. At the end of this time the reaction was quenched with 10% AcOH in methanol and the solvent was removed under reduced pressure. The crude product thus obtained was diluted with CHCl3 and washed with water, dried (CaCl2) and the solvent was removed under reduced pressure to get 11.5 g (81%) of the title compound as a thick liquid.

Workup

  1. customAt the end of this time the reaction was quenched with 10% AcOH in methanol
  2. customthe solvent was removed under reduced pressure
  3. customThe crude product thus obtained
  4. washwashed with water
  5. dry with materialdried (CaCl2)
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dc2d9d5883524716b91b81109ef78163
Source dataset
uspto-grants-1999_03
Patent number
US05889025

Reaction notes

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