Sodium borohydride → HCID 67740419, compound

HRID 580995Notes

Reaction equation

HRID 580995 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2([OH:21])[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[C:7]([CH2:22][CH:23]=[CH2:24])[CH:6]=1)=O.Cl.[CH3:26][NH2:27]>C(O)C.[OH-].[Na+]>[CH3:26][NH:27][CH2:3][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2([OH:21])[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[C:7]([CH2:22][CH:23]=[CH2:24])[CH:6]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 6364545Methylamine hydrochlorideHCID 54248308HCID 54248308, compound

Product 1

HCID 67740419HCID 67740419, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
5 °C

Procedure

Sodium borohydride (380 mg) was added to a solution of 3-[2-(4-formyl-2-allylphenyl)ethynyl]quinuclidine-3-ol (2.95 g) and methylamine hydrochloride (1.01 g) in ethanol (50 ml) whilst maintaining the temperature at 5° C. The resulting mixture was stirred at 25° C. for 12 hours, filtered and the filtrate evaporated to leave a residue which was suspended in 1M aqueous sodium hydroxide solution (30 ml) and extracted with ethyl acetate (3×50 ml). The ethyl acetate extracts were combined, washed with brine (50 ml), dried (Na2SO4) and evaporated. The residue was triturated with diethyl ether to give 3-[2-(4-methylaminomethyl-2-allylphenyl)ethynyl]quinuclidin-3-ol as a solid, m.p. 80° C.; microanalysis, found C, 75.1; H, 8.3; N, 8.6%; C20H26N2O.0.5H2O requires: C, 75.2; H, 8.5; N, 8.8%; NMR (CDCl3): 1.4 (-1H, m), 1.65 (1H, m), 2.1 (5H, m), 2.5 (3H, s), 2.8 (4H, t), 3.1 (1H, d), 3.3 (1H, dd), 3.5 (2H, d), 3.7 (2H, s), 5.1 (4H, m), 5.9 (1H, m), 7.1 (2H, m) and 7.4 (1H, d), m/z 311 (M+H).

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated
  3. customto leave a residue which
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washwashed with brine (50 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-e06bbad662f24ac69cf9f1d42360034e
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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