Ethanol → (3R,4S)-1-(4-amino-3-methoxyphenyl)-3-fluoropiperidin-4-amine

HRID 1256018Notes

Reaction equation

HRID 1256018 reaction equation
C(O)C.C([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[C:20]([O:27][CH3:28])[CH:19]=2)[CH2:14][C@H:13]1[F:29])C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([N:15]2[CH2:16][CH2:17][C@H:12]([NH2:11])[C@H:13]([F:29])[CH2:14]2)=[CH:19][C:20]=1[O:27][CH3:28]

Participants

5

Reactant 2

HCID 702EthanolHCID 58071500(3R,4S)-N-benzyl-3-fluoro-1-(3-methoxy-4-nitrophenyl)piperidin-4-amine2×

Product 1

HCID 58071469(3R,4S)-1-(4-amino-3-methoxyphenyl)-3-fluoropiperidin-4-amineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethanol (15 ml) and ethyl acetate (3.00 ml) were added to a flask charged with (3R,4S)—N-benzyl-3-fluoro-1-(3-methoxy-4-nitrophenyl)piperidin-4-amine (INTERMEDIATE 47) (1.4 g, 3.90 mmol) and Pd/C (0.415 g, 0.39 mmol). The flask was degassed and filled with H2. The reaction was stirred at RT for 2 h under hydrogen balloon. The reaction mixture was filtered through a pad of Celite® and the filtrate was concentrated under reduced pressure to give the title product (0.840 g, 90%).

Workup

  1. customThe flask was degassed
  2. additionfilled with H2
  3. filtrationThe reaction mixture was filtered through a pad of Celite®
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-909fc0c9db034185bd7b2643a672ee57
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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