Benzyl chloroformate → Cbz-L-Prolinol

HRID 917652Notes

Reaction equation

HRID 917652 reaction equation
[C:1](Cl)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[NH:12]1[CH2:18][CH2:17][CH2:16][C@H:13]1[CH2:14][OH:15].C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[C:1]([N:12]1[CH2:18][CH2:17][CH2:16][C@H:13]1[CH2:14][OH:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 640091L-Prolinol

Product 1

HCID 11096562Cbz-L-ProlinolYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of carbobenzoxychloride 7.87 g in methylene chloride 50 ml is dropped to a mixture of L-prolinol 4.9 g in methylene chloride 50 ml and sodium hydrogen carbonate 11.6 g in water 50 ml at 0° C. under vigorously agitation. The mixture is stirred for 1 hour at room temperature. The organic layer is separated, washed, dried and concentrated in vacuo to give N-carbobenzoxy-L-prolinol 10.25 g.

Workup

  1. customThe organic layer is separated
  2. washwashed
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a825d514598d4e6b9e6e7dba91978fc7
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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