Ammonia → 3-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]pyridine

HRID 617286Notes

Reaction equation

HRID 617286 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C@H:3]1CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[OH:41][C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1.N>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C@H:7]1[CH2:6][O:41][C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 70070172HCID 70070172, compound

Product 1

HCID 97941413-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]pyridineYield 31%

Procedure

(S)-1-Methyl-2-pyridinemethanol was reacted with triphenylphosphine, DEAD and 3-hydroxypyridine according to the procedure outlined in Example 1a The crude product was purified by flash chromatography (2×) using (10% MeOH/CHCl3) to remove the diethyl hydrazine dicarboxylate impurity and give a yellow oil in 31% yield. MS (DCI/NH3) m/e 193 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.32 (t, J=1.5 Hz, 1H), 8.22 (t, J=3 Hz, 1H), 7.24-7.2 (m, 2H), 4.14-4.05 (dd, J=9, 6 Hz, 1H), 4.00-3.93 (dd, J=9, 6 Hz, 1H), 3.243.14 (m, 1H, 2.81-2.7 (m, 1H), 2.54 (s, 3H), 2.44-2.31 (m, 1H, 2.14-2.00 (m, 1H, 1.96-1.71 (m, 3H).

Workup

  1. customwas purified by flash chromatography (2×)
  2. customto remove the diethyl hydrazine dicarboxylate impurity
  3. customgive a yellow oil in 31% yield

Sources & evidence

ORD record
ord-8470452dc145482194aa969a91e67320
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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