Sodium borohydride → 3-Diphenylmethyl-1,2,3,6-tetrahydropyridin-1-yl acetic acid ethyl ester

HRID 611551Notes

Reaction equation

HRID 611551 reaction equation
[Br-].[CH2:2]([O:4][C:5]([CH2:7][N+:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)=[O:6])[CH3:3].[BH4-].[Na+]>>[CH2:2]([O:4][C:5](=[O:6])[CH2:7][N:8]1[CH2:13][CH:12]=[CH:11][CH:10]([CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)[CH3:3]

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 158705841-Ethoxycarbonylmethyl-3-diphenylmethylpyridinium bromide

Product 1

HCID 158705863-Diphenylmethyl-1,2,3,6-tetrahydropyridin-1-yl acetic acid ethyl esterYield 64%

Procedure

To an ice cooled solution of 0.206 g (0.5 mmol) 1-ethoxycarbonylmethyl-3-diphenylmethylpyridinium bromide (from step 1) was added 0.034 g (0.92 mmol) sodium borohydride in small portions with stirring over one hour. The solvent was evaporated, the residue dissolved in diethyl ether, washed with water and dried with magnesium sulphate. After evaporation of the solvent, the residue was chromatographed on silica gel column with 30% ethyl acetate in hexanes to give 0.107 g (64%) 3-diphenylmethyl-1,2,3,6-tetrahydropyridin-1-yl acetic acid ethyl ester (compound C1) as a pale yellow oil. NMR spectra showed: 1H NMR (CDCl3, 300 MHz) δ 7.40-7.10 (m, 10 H), 5.22 (br. s,1 H), 4.61 (s, 1 H), 4.12 (q, 2 H), 3.25 (s, 2 H), 3.03 (s, 2 H), 2.68 (t, 2 H), 2.22 (br. s, 2 H), 1.19 (t, 3 H); 13C NMR (CDCl3 75 MHz) δ 170.24, 141.86, 137.89, 129.11, 128.10, 126.19, 123.24, 60.31, 58.79, 56.24, 55.13, 49.51, 25.64, 14.05. El-MS: 335 (10, M+, C22H25NO2), 262 (50).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in diethyl ether
  3. washwashed with water
  4. dry with materialdried with magnesium sulphate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel column with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c0f9efb40b0142d8a4b970f37bfb110f
Source dataset
uspto-grants-1999_12
Patent number
US06001854

Reaction notes

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