Hydrochloric Acid → HCID 86755495, compound

HRID 2287513Notes

Reaction equation

HRID 2287513 reaction equation
[ClH:1].[CH2:2]([O:9][CH2:10][C@@H:11]1[C@@H:15]([CH3:16])[NH:14][C@@H:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:12]1[NH:23][CH2:24][C:25]1[CH:30]=[C:29]([CH:31]([CH3:33])[CH3:32])[CH:28]=[CH:27][C:26]=1[O:34][CH3:35])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[ClH:1].[ClH:1].[CH2:2]([O:9][CH2:10][C@@H:11]1[C@@H:15]([CH3:16])[NH:14][C@@H:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:12]1[NH:23][CH2:24][C:25]1[CH:30]=[C:29]([CH:31]([CH3:32])[CH3:33])[CH:28]=[CH:27][C:26]=1[O:34][CH3:35])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15454943HCID 15454943, compound

Product 1

HCID 86755495HCID 86755495, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An excess amount of Hydrogen Chloride, Methanol Reagent 10 (Tokyo Kasei) was added to (2S*,3S*,4R*,5R*)-4-benzyloxymethyl-3-[N-(5-isopropyl-2-methoxybenzyl)amino]-5-methyl-2-phenylpyrrolidine (0.40 g, 0.87 mmol) until the mixture became acidic. The solvent MeOH was evaporated in vacuo, and the syrupy residue was crystallized from EtOH--Et2O to give title compound (0.40 g, 87%) as white powders (mp 129-133 C.): IRmax (nujol): 3450(w), 3100-2100(br.s), 1510(s), 1255(s), 1087(m), 810(w), 755(m), 700(s) cm-1 ; 1H-NMR δ (DMSO-d6): 7.83(br.s, 2H), 7.62-7.40(m, 3H), 7.40-7.33(m, 4H), 7.37-7.25(m, 1H), 7.25-7.12(m, 2H), 6.89(d, J=8.4 Hz, 1H), 5.11(br.s, 1H), 4.59(s, 2H), 3.78-3.50(m, 5H), 3.67(br.s, 2H), 3.45-3.30[m, 3H; overlaped with the signals (δ 3.35) due to H2O], 3.35[s, 3H; overlaped with the signals (δ 3.35) due to H2O], 2.77(sep, J=7.0 Hz, 1H), 2.55-2.48[m, 1H; overlaped with the signals (δ 2.50) due to DMSO], 1.64(br.d, J=5.9 Hz, 3H), 1.14(d, J=7.0 Hz, 6H) ppm.

Workup

  1. customThe solvent MeOH was evaporated in vacuo
  2. customthe syrupy residue was crystallized from EtOH

Sources & evidence

ORD record
ord-7cf82eb349b648ecae4c39104cec4ef0
Source dataset
uspto-grants-2000_07
Patent number
US06083943

Reaction notes

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