1,1-Bis(4-hydroxyphenyl)-2-phenylbut-1-ene → HCID 123259535, compound

HRID 626121Notes

Reaction equation

HRID 626121 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH3:11])=[CH:4][CH:3]=1.O[C@H:26]1[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[C:12]1([C:9]([CH2:10][CH3:11])=[C:8]([C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)[C:5]2[CH:6]=[CH:7][C:2]([O:1][C@@H:26]3[CH2:30][CH2:29][NH:28][CH2:27]3)=[CH:3][CH:4]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 630591,1-Bis(4-hydroxyphenyl)-2-phenylbut-1-eneHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylateHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 123259535HCID 123259535, compoundYield 20%

Procedure

Following the same procedure as described in example 16, step D & E, 4-(1-(4-hydroxylphenyl)-2-phenylbut-1-enyl)phenol (150 mg, 0.474 mmol) was reacted with (S)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (107 mg, 0.571 mmol), followed by de-Boc in condition of TFA/CH2Cl2, to give the desired product (36 mg, 20% yield, Z/E=1/1). m/z=386[M+1]+.

Sources & evidence

ORD record
ord-1ca1171e682c4a5fbab5f0059f9d2a01
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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