Benzyl chloroformate → HCID 18991262, compound

HRID 1648375Notes

Reaction equation

HRID 1648375 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O.CC(O)=O.[Rh]>[C:21]([N:1]1[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH:3]([C:10]([OH:12])=[O:11])[CH2:2]1)([O:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:22]

Participants

6

Reactant 2

HCID 10387Benzyl chloroformateHCID 69867Indole-3-Carboxylic Acid

Product 1

HCID 18991262HCID 18991262, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 25 g (155 mmol) of indole-3-carboxylic acid in 1500 mL H2O and 150 mL HOAc was charged with 25 g of 5% Rh/Al2O3 and the mixture hydrogenated at 60 psi for 30 hr at 60° C. The mixture was filtered through Celite® and evaporated in vacuo to a dark oil which was treated with benzylchloroformate (26.35 g; 155 mmol) under basic conditions substantially according to the procedures of Example 15, A. The crude product crystallized out of hot CH2Cl2 /hexanes to yield 16.06 g (53 mmol; 49%) of N-Cbz-3-perhydroindolylcarboxylic acid as a white solid.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customevaporated in vacuo to a dark oil which
  3. customThe crude product crystallized out of hot CH2Cl2 /hexanes

Sources & evidence

ORD record
ord-6e1be4fa079245ccaa7943e2342d0517
Source dataset
uspto-grants-1995_07
Patent number
US05436229

Reaction notes

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