Water → HCID 22128821, compound

HRID 1858721Notes

Reaction equation

HRID 1858721 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:14][CH:13]3[NH:15][CH:10]([CH2:11][CH2:12]3)[CH:9]2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:25]([C:30]([O:32]C)=O)=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[CH3:41]COCC>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:14][CH:13]3[NH:15][CH:10]([CH2:11][CH2:12]3)[CH:9]2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH:30]([OH:32])[CH3:41])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 3283Diethyl Ether3×HCID 21226445Aluminium lithium hydrideHCID 131721773HCID 131721773, compound

Product 1

HCID 22128821HCID 22128821, compoundYield 68%

Procedure

A solution of 0.330 g (0.71 mmol) of methyl (1RS,2RS,3RS,5SR)-4'-[3-(4-chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-yloxymethyl]-biphenyl-2-carboxylate in 10 ml of ether was slowly added dropwise to a suspension of 33 mg of lithium aluminium hydride in 5 ml of ether and the mixture was stirred at room temperature for 4 hours. After the addition of aqueous ether and subsequently water the phases were separated, the organic phase was washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and evaporated. The residue was chromatographed on silica gel using a 140:10:1 mixture of methylene chloride, methanol and ammonia as the eluent. There was obtained 0.210 g (68% of theory) of [4'-[3-(4-chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-yloxymethyl]-biphenyl-2-yl]-ethanol as a colourless foam, Rf : 0.18 (methylene chloride:methanol:ammonia=140:10:1), MS: 434 (M+H)+.

Workup

  1. customwere separated
  2. washthe organic phase was washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica gel using
  7. additiona 140:10:1 mixture of methylene chloride, methanol and ammonia as the eluent

Sources & evidence

ORD record
ord-5959ecceedaf4514bc4acc4f3c37f27a
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

Loading…