Hydrochloric Acid → 1-{[(1S,3R)-3-Amino-1-isopropylcyclopentyl]carbonyl}-4-[2-(trifluoromethyl)phenyl]piperidin-4-ol

HRID 1261655Notes

Reaction equation

HRID 1261655 reaction equation
[OH:1][C:2]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([F:35])([F:34])[F:33])[CH2:7][CH2:6][N:5]([C:8]([C@@:10]2([CH:23]([CH3:25])[CH3:24])[CH2:14][CH2:13][C@@H:12]([NH:15]C(=O)OC(C)(C)C)[CH2:11]2)=[O:9])[CH2:4][CH2:3]1.Cl>CCOCC>[NH2:15][C@@H:12]1[CH2:13][CH2:14][C@@:10]([C:8]([N:5]2[CH2:6][CH2:7][C:2]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:33])[F:34])([OH:1])[CH2:3][CH2:4]2)=[O:9])([CH:23]([CH3:25])[CH3:24])[CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59833553tert-Butyl [(1R,3S)-3-({4-hydroxy-4-[2-(trifluoromethyl)phenyl]piperidin-1-yl}carbonyl)-3-isopropylcyclopentyl]carbamate

Product 1

HCID 579387311-{[(1S,3R)-3-Amino-1-isopropylcyclopentyl]carbonyl}-4-[2-(trifluoromethyl)phenyl]piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a flask containing tert-butyl {(1R,3S)-3-({4-hydroxy-4-[2-(trifluoromethyl)phenyl]piperidin-1-yl}carbonyl)-3-isopropylcyclopentyl]carbamate (0.27 g, 0.54 mmol) was added a 2.00 M solution of HCl in ether (5 mL) and the resulting mixture stirred for 3.5 h. The solution was concentrated to give an oil which was used in the next reaction without purification. MS calculated for C21H29F3N2O2: (M+H) 399; found 399.2.

Workup

  1. concentrationThe solution was concentrated
  2. customto give an oil which
  3. customwas used in the next reaction without purification

Sources & evidence

ORD record
ord-32d7bde93694404eb246af7a7be8fd11
Source dataset
uspto-grants-2013_06
Patent number
US08470827B2

Reaction notes

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