Triphenylphosphine → HCID 68323590, compound

HRID 1748299Notes

Reaction equation

HRID 1748299 reaction equation
O[CH2:2][C:3]1([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:6][CH2:5][CH2:4]1.[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:23]=2)[CH:18]=[C:17]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:11]([O:10][C:9]([NH:8][CH2:7][C:3]1([CH2:2][N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:23]=3)[CH:18]=[C:17]2[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:6][CH2:5][CH2:4]1)=[O:15])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 44754779Diethyl 1H-indole-2,6-dicarboxylateHCID 68323591HCID 68323591, compound

Product 1

HCID 68323590HCID 68323590, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl {[1-(hydroxymethyl)cyclobutyl]methyl}carbamate (12 g, 55.76 mmol), diethyl 1H-indole-2,6-dicarboxylate (14.56 g, 55.76 mmol) and triphenylphosphine (29.2 g, 111.5 mmol.) in THF (110 mL) is added diisopropyl azodicarboxylate (22.41 mL, 111.5 mmol) at room temperature and the reaction mixture is stirred for 60 h. The solvent is evaporated and the residue is purified by flash column chromatography using 12% EtOAc in petroleum ether to afford diethyl 1-[(1-{[(tert-butoxycarbonyl)amino]methyl}cyclobutyl)methyl]-1H-indole-2,6-dicarboxylate contaminated with un-reacted diethyl 1H-indole-2,6-dicarboxylate. The mixture is used in the next step without further purification.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-69731bac2b28448cbc9ecb7c74e67e6d
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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