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

HRID 525585Notes

Reaction equation

HRID 525585 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][NH:28][CH2:29][CH3:30])=[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][NH:28][CH2:29][CH3:30])=[CH:25][CH:26]=2)=[CH:19][CH:20]=1)[OH:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86695464(4S,5R)-5-[4-(6-Ethylaminomethyl-pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 86695465(1S,2S)-2-Amino-1-[4-(6-ethylaminomethyl-pyridin-3-yl)-phenyl]-3-fluoro-propan-1-olYield 117.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4S,5R)-5-[4-(6-Ethylaminomethyl -pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.05 g, 0.112 mmol) in CH2Cl2 (0.2 mL) is added trifluoroacetic acid (0.2 mL) at 0° C. Reaction mixture allowed to warm to room temperature and stirred for 2 hours. The volatiles were removed under reduced pressure to obtain crude material purified by column chromatography eluting in 10% methanol in CH2Cl2 to afford crude title compound (0.04 g, crude). LC-MS (m/z): [M+H]=304.2.

Workup

  1. customReaction mixture
  2. customThe volatiles were removed under reduced pressure
  3. customto obtain crude material
  4. custompurified by column chromatography
  5. washeluting in 10% methanol in CH2Cl2

Sources & evidence

ORD record
ord-b7717cfe67b64fa4a615a131980c4983
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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