Tetrabutylammonium Fluoride → 2-[2-(4-methoxycarbonylmethylphenoxy)-1(R)methylethyl]amino-1(R)-(3-chlorophenyl)ethanol

HRID 1682729Notes

Reaction equation

HRID 1682729 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]1[CH:33]=[CH:32][C:9]([O:10][CH2:11][C@H:12]([NH:14][CH2:15][C@H:16]([O:24][Si](C(C)(C)C)(C)C)[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[CH3:13])=[CH:8][CH:7]=1)=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]([CH2:5][C:6]1[CH:33]=[CH:32][C:9]([O:10][CH2:11][C@H:12]([NH:14][CH2:15][C@@H:16]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[OH:24])[CH3:13])=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22873128N-[2-(4-Methoxycarbonylmethylphenoxy)-1(R)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-(3-chlorophenyl)ethanamine

Product 1

HCID 228670762-[2-(4-methoxycarbonylmethylphenoxy)-1(R)methylethyl]amino-1(R)-(3-chlorophenyl)ethanolYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 27, but using 3.02 g of N-[2-(4-methoxycarbonylmethylphenoxy)-1(R)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-(3-chlorophenyl)ethanamine (prepared as described in Preparation 50), 4.81 g of tetrabutylammonium fluoride and 100 ml of tetrahydrofuran, 1.7 g of the title compound were obtained having an Rf=0.39 (thin layer chromatography over silica gel, using ethyl acetate as the developing solvent). [α]D23 -13.2° (c=0.99, methanol).

Sources & evidence

ORD record
ord-bd834f8f90f049cd876e56866c0a84f2
Source dataset
uspto-grants-1997_06
Patent number
US05635534

Reaction notes

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