Water → Ammonia

HRID 1858602Notes

Reaction equation

HRID 1858602 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:23]=[CH:22][C:17]([C:18](OC)=[O:19])=[CH:16][CH:15]=2)[CH:10]([OH:24])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].O>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([CH2:18][OH:19])=[CH:22][CH:23]=2)[CH:10]([OH:24])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[NH3:8]

Participants

6

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 54060721HCID 54060721, compound

Product 2

HCID 222AmmoniaHCID 22126993HCID 22126993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5.0 g (15.3 mmol) of methyl (3RS,4RS)-4-(1-benzyl-3-hydroxy-piperidin-4-yl)-benzoate in 50 ml of tetrahydrofuran was treated at room temperature with 720 mg (32.9 mmol) of lithium borohydride. Subsequently, the reaction mixture was heated to 60° C. for 15 hours. For the working-up, the reaction mixture was treated with 20 ml of water while cooling with ice and thereafter extracted twice with 50 ml of ethyl acetate each time. The organic phases were combined, dried over sodium sulphate and evaporated under reduced pressure. The crude (3RS,4RS)-1-benzyl-4-(4-hydroxymethyl-phenyl)-piperidine-3-ol obtained (Rf: 0.23, methylene chloride:methanol:ammonia=95:5:0.1) was used in the following step without further purification.

Workup

  1. temperaturewhile cooling with ice
  2. extractionextracted twice with 50 ml of ethyl acetate each time
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2a18dc9e1a4b4b30a6f23f514be47046
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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