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

HRID 1901174Notes

Reaction equation

HRID 1901174 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 22867087N-[2-(4-methoxycarbonylmethylphenoxy)-1(S)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-phenylethanamine

Product 1

HCID 228670782-[2-(4-Methoxycarbonylmethylphenoxy)-1(S)-methylethyl]amino-1(R)-phenylethanolYield 66.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 27, but using 460 mg of N-[2-(4-methoxycarbonylmethylphenoxy)-1(S)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-phenylethanamine (prepared as described in Preparation 31), 15 ml of tetrahydrofuran and 780 mg of tetrabutylammonium fluoride, 0.23 g of the title compound was obtained as crystals, melting at 89°-90° C.

Sources & evidence

ORD record
ord-1e314bb2521d4498b6b57546ee406531
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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