Tri-o-tolylphosphine → 3-(1-Benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-(3-hydroxymethylphenyl)-1H-indole

HRID 1441072Notes

Reaction equation

HRID 1441072 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([Sn](CCCC)(CCCC)CCCC)[CH:6]=[CH:7][CH:8]=1.[CH2:22]([O:29][C:30]([N:32]1[CH2:36][CH2:35][CH2:34][C@@H:33]1[CH2:37][C:38]1[C:46]2[C:41](=[CH:42][CH:43]=[C:44](Br)[CH:45]=2)[NH:40][CH:39]=1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH2:22]([O:29][C:30]([N:32]1[CH2:36][CH2:35][CH2:34][C@@H:33]1[CH2:37][C:38]1[C:46]2[C:41](=[CH:42][CH:43]=[C:44]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=3)[CH:45]=2)[NH:40][CH:39]=1)=[O:31])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 22420944HCID 22420944, compoundHCID 22859561(R)-Benzyl 2-((5-bromo-1H-indol-3-yl)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 228595573-(1-Benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-(3-hydroxymethylphenyl)-1H-indoleYield 51.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

3-Hydroxymethylphenyltri-n-butylstannane (2.016 g, 5.076 mmol) (see Preparation 25) and 3-(1-benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-bromo-1H-indole (1.902 g, 4.602 mmol) (see Preparation 35B) were reacted together in the presence of tri-o-tolylphosphine, triethylamine and palladium (II) acetate using a procedure similar to that described in Example 1. This yielded the title compound as a white foam (1.050 g). Found: C,75.58; H,6.51; N,5.88; C28H28N2O3.1/12CH2Cl2 requires: C,75.36; H,6.34; N,6.26%.

Sources & evidence

ORD record
ord-4cfb60e2c21d403ca67ae06afde5b005
Source dataset
uspto-grants-1996_03
Patent number
US05502065

Reaction notes

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