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

HRID 1436775Notes

Reaction equation

HRID 1436775 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-ce2757be35bf4a3abe9e8414697a4564
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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