Water → Ammonia

HRID 1004983Notes

Reaction equation

HRID 1004983 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 tetra-hydrofuran was treated at room temperature with 720 mg (32.9 mmol) of lithium borohydride. Subsequently, the reaction mixture was heated to 60° C. for 1 5 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-1ca369d496a14bbaab65b7f9c6a091c6
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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