Isobutyl chloroformate → HCID 67422161, compound

HRID 880713Notes

Reaction equation

HRID 880713 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].FC(F)(F)C([O-])=O.[CH2:16]([O:23][C:24]1[CH:29]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=[CH:26][C:25]=1[CH:38]1[CH2:42][CH2:41][NH2+:40][CH2:39]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1.C(N(CC)C(C)C)(C)C>[CH2:5]([O:4][C:2]([N:40]1[CH2:41][CH2:42][CH:38]([C:25]2[CH:26]=[CH:27][C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:29][C:24]=2[O:23][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:39]1)=[O:3])[CH:6]([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 62365Isobutyl chloroformateHCID 67423062HCID 67423062, compound

Product 1

HCID 67422161HCID 67422161, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 81531DiisopropylethylamineSolvent

Procedure

In a 10 ml round-bottomed flask, 0.25 g of 3-(2,4-bis(benzyloxy)phenyl)pyrrolidinium trifluoroacetate is dissolved in 5 ml of tetrahydrofuran in the presence of 0.25 ml of N,N-diisopropylethylamine. 0.108 g of isobutyl chloroformate is added and the reaction mixture is stirred for 30 minutes at ambient temperature. The reaction mixture is extracted with ethyl acetate and the organic phases are then combined and dried over magnesium sulphate. The residue is chromatographed on silica gel (8/2 heptane/ethyl acetate). 0.22 g of 3-(2,4-bis(benzyloxy)phenyl)pyrrolidine-1-carboxylic acid isobutyl ester is obtained. Yield=66%.

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate
  2. dry with materialdried over magnesium sulphate
  3. customThe residue is chromatographed on silica gel (8/2 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-f065fce0892a4957a10b1150707bd743
Source dataset
uspto-grants-2015_03
Patent number
US08993596B2

Reaction notes

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