Tetrabutylammonium Fluoride → 2-[2-(4-Methoxycarbonylmethylphenoxy)-1(R)-methylethyl]amino-1(S)-phenylethanol

HRID 1682717Notes

Reaction equation

HRID 1682717 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]1[CH:32]=[CH:31][C:9]([O:10][CH2:11][C@H:12]([NH:14][CH2:15][C@@H:16]([O:23][Si](C(C)(C)C)(C)C)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][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:32]=[CH:31][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]=[CH:19][CH:18]=2)[OH:23])[CH3:13])=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22867086N-[2-(4-methoxycarbonylmethylphenoxy)-1(R)-methylethyl]-2(S)-t-butyldimethylsilyloxy-2-phenylethanamine

Product 1

HCID 228670772-[2-(4-Methoxycarbonylmethylphenoxy)-1(R)-methylethyl]amino-1(S)-phenylethanolYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 27, but using 880 mg of N-[2-(4-methoxycarbonylmethylphenoxy)-1(R)-methylethyl]-2(S)-t-butyldimethylsilyloxy-2-phenylethanamine (prepared as described in Preparation 32), 20 ml of tetrahydrofuran and 1.5 g of tetrabutylammonium fluoride, 0.5 g of the title compound was obtained as crystals, melting at 90°-91° C.

Sources & evidence

ORD record
ord-e8d4ea513c4f4270aaabc75356520ec3
Source dataset
uspto-grants-1997_06
Patent number
US05635534

Reaction notes

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