Butyl iodide → (3R,4R,5R)-3-benzyloxy-1-butyl-5-hydroxymethyl-4-piperidinol

HRID 1003375Notes

Reaction equation

HRID 1003375 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([OH:15])[C@@H:13]([CH2:16][OH:17])[CH2:12][NH:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:19][CH2:20][CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:8][C@H:9]1[C@H:14]([OH:15])[C@@H:13]([CH2:16][OH:17])[CH2:12][N:11]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 15235481(3R,4R,5R)-3-Benzyloxy-5-hydroxymethyl4-piperidinol

Product 1

HCID 53945335(3R,4R,5R)-3-benzyloxy-1-butyl-5-hydroxymethyl-4-piperidinolYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(3R,4R,5R)-3-Benzyloxy-5-hydroxymethyl-4-piperidinol (87 mg, 0.37 mmol), 1-iodobutane (81 mg, 0.44 mmol, 50 μl), potassium carbonate (154 mg, 1.1 mmol) and dry acetone (8 ml) were stirred for 24h at 40° C. under a nitrogen atmosphere. The solvent was evaporated in vacuo, and the residue purified on a silica gel column (Eluent: ethyl acetate/methanol/25% ammonium hydroxide (6/1/1%)). This afforded the free base of (3R,4R,5R)-3-benzyloxy-1-butyl-5-hydroxymethyl-4-piperidinol (Yield: 72 mg, 67%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue purified on a silica gel column (Eluent: ethyl acetate/methanol/25% ammonium hydroxide (6/1/1%))

Sources & evidence

ORD record
ord-e8460faa1850473bbc1380ff3efb8b38
Source dataset
uspto-grants-2000_04
Patent number
US06046214

Reaction notes

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