Trifluoroacetic acid → (1S,2S)-2-Amino-1-[4-(6-dimethylaminomethyl-pyridin-3-yl)-phenyl]-3-fluoro-propan-1-ol

HRID 1487524Notes

Reaction equation

HRID 1487524 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][F:14])[C@@H:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[N:23][C:24]([CH2:27][N:28]([CH3:30])[CH3:29])=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[O:10]C1(C)C)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C@H:12]([CH2:13][F:14])[C@H:11]([C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:22]=[N:23][C:24]([CH2:27][N:28]([CH3:29])[CH3:30])=[CH:25][CH:26]=2)=[CH:19][CH:20]=1)[OH:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86695470(4S,5R)-5-[4-(6-Dimethylaminomethyl-pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 86695472(1S,2S)-2-Amino-1-[4-(6-dimethylaminomethyl-pyridin-3-yl)-phenyl]-3-fluoro-propan-1-olYield 109.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4S,5R)-5-[4-(6-Dimethylaminomethyl-pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (80 mg, 0.180 mmol) in CH2Cl2 (0.32 mL) is added trifluoroacetic acid (0.32 mL). Reaction mixture allowed to warm to room temperature and stirred for 2 hours. The volatiles are removed under reduced pressure to obtain crude material purified by column chromatography eluting in 40% methanol in CH2Cl2 to afford the title compound (60 mg). LC-MS (m/z): [M+H]=304.1.

Workup

  1. customReaction mixture
  2. customThe volatiles are removed under reduced pressure
  3. customto obtain crude material
  4. custompurified by column chromatography
  5. washeluting in 40% methanol in CH2Cl2

Sources & evidence

ORD record
ord-087f31b2e094449fb79c6d05389d7dd5
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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