Trifluoroacetic acid → (R)-Phenyl[(2R,5S)-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidin-2-yl]methanol

HRID 1804651Notes

Reaction equation

HRID 1804651 reaction equation
[OH:1][C@H:2]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C@H:3]1[CH2:7][CH2:6][C@@H:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:19][CH2:18]3)=[O:16])=[CH:11][CH:10]=2)[N:4]1C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[C:37]1([C@H:2]([C@H:3]2[CH2:7][CH2:6][C@@H:5]([CH2:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]([N:17]4[CH2:18][CH2:19][N:20]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=5)[CH2:21][CH2:22]4)=[O:16])=[CH:11][CH:10]=3)[NH:4]2)[OH:1])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86666758Tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidine-1-carboxylate

Product 1

HCID 67972431(R)-Phenyl[(2R,5S)-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidin-2-yl]methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.038 g (0.067 mmol) of the title compound from Step A above in 1 mL dichloromethane and 1 mL trifluoroacetic acid was stirred at ambient temperature for 1 h. All volatiles were removed in vacuo and the crude light brown residue was purified directly by reverse-phase HPLC to afford the title compound (TMC Pro-Pac C18; 10-100% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). 1H-NMR (500 MHz, CD4O) δ 8.70 (d, J=4.9 Hz, 1H), 7.99-7.98 (m, 1H), 7.59 (d, J=7.8 Hz, 1H), 7.53-7.34 (m, 10H), 4.76 (d, J=8.8 Hz, 1H), 4.51 (s, 2H), 4.10-3.81 (m, 6H), 3.42-3.39 (m, 4H), 3.33-3.08 (m, 2H), 2.10-2.00 (m, 1H), 1.86-1.75 (m, 3H). LC/MS: m/z (ES) 471.3 (MH)+, 493.3 (MNa)+.

Workup

  1. customAll volatiles were removed in vacuo
  2. customthe crude light brown residue was purified directly by reverse-phase HPLC

Sources & evidence

ORD record
ord-6bcf9631a2a74e8695e4670078a7984f
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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