((2R)-1-methylpyrrolidin-2-yl)methanol → 2(R)-(3-Fluorophenoxymethyl)-1-methylpyrrolidine hydrochloride

HRID 2259199Notes

Reaction equation

HRID 2259199 reaction equation
CN1CCC[C@@H]1CO.[ClH:9].[F:10][C:11]1[CH:12]=[C:13]([CH:22]=[CH:23][CH:24]=1)[O:14][CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[CH3:21]>O>[ClH:9].[F:10][C:11]1[CH:12]=[C:13]([CH:22]=[CH:23][CH:24]=1)[O:14][CH2:15][C@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[CH3:21]

Participants

4

Reactant 2

HCID 11007868((2R)-1-methylpyrrolidin-2-yl)methanolHCID 228577072(S)-(3-Fluorophenoxymethyl)-1-methyl-pyrrolidine hydrochloride

Product 1

HCID 228577012(R)-(3-Fluorophenoxymethyl)-1-methylpyrrolidine hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following the procedures of Example 6, substituting (R)-1-methyl-2-pyrrolidinemethanol (Aldrich) for the (S)-1-methyl-2-pyrrolidinemethanol of Example 6, the title compound was prepared. MS: 210 (M+H)+. NMR (CDCl3) δ: 2.20-2.30 (m, 3H), 2.34-2.43 (m, 1H), 3.03 (s, 3H), 3.20-3.30 (m, 1H), 3.72-3.77 (m, 1H), 3.89-3.91 (m, 1H), 4.27 (dd, 1H, J=6, 11.5 Hz), 4.44 (dd, 1H, J=3, 11.5 Hz), 6.82-6.89 (m, 3H), 7.34-7.42 (m, 1H). Anal. Calcd for C12H17ClFNO.0.25 H2O: C, 57.60; H, 7.05; N, 5.59; Found: C, 57.86; H, 6.76; N, 5.59.

Sources & evidence

ORD record
ord-b48cc0c285b647e69fcd6c08b59efea8
Source dataset
uspto-grants-1995_12
Patent number
US05472958

Reaction notes

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