Trifluoroacetic acid → (S)-2-amino-5-(4-chloro-phenyl)-5-methoxy-pentan-1-ol

HRID 885196Notes

Reaction equation

HRID 885196 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][CH2:14][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[O:16][CH3:17])[CH2:11][O:10]C1(C)C)=O)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:8][C@@H:12]([CH2:13][CH2:14][CH:15]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[O:16][CH3:17])[CH2:11][OH:10]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59173153(S)-4-[3-(4-chloro-phenyl)-3-methoxy-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 59173183(S)-2-amino-5-(4-chloro-phenyl)-5-methoxy-pentan-1-ol

Procedure

In analogy to example 45c (S)-4-[3-(4-chloro-phenyl)-3-methoxy-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester was reacted with trifluoroacetic acid to give (S)-2-amino-5-(4-chloro-phenyl)-5-methoxy-pentan-1-ol. Yellow oil. MS (ISP): 246.1 ([{37Cl}M+H]+), 244.1 ([{35Cl}M+H]+).

Sources & evidence

ORD record
ord-252e0ebfe3674bdb90566c083bc7b8e1
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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