Tetrabutylammonium Fluoride → (3RS,4RS)-4-(3-bromophenyl)-piperidin-3-ol

HRID 1004929Notes

Reaction equation

HRID 1004929 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][N:11](C(OCC[Si](C)(C)C)=O)[CH2:10][CH:9]2[O:23]C(OCC[Si](C)(C)C)=O)[CH:5]=[CH:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]2[OH:23])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 539146402-trimethylsilylethyl (3RS,4RS)-4-(3-bromophenyl)-3-(2-trimethylsilyl-ethoxycarbonyloxy)-piperidine-1-carboxylate

Product 1

HCID 22126337(3RS,4RS)-4-(3-bromophenyl)-piperidin-3-olYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 470 mg (0.863 mmol) of 2-trimethylsilylethyl (3RS,4RS)-4-(3-bromophenyl)-3-(2-trimethylsilyl-ethoxy-carbonyloxy)-piperidine-1-carboxylate in 3 ml of absolute tetrahydrofuran was treated with 2.65 ml (2.91 mmol) of tetrabutylammonium fluoride solution (1.1 M in THF) and stirred at room temperature for 2.5 hours. Subsequently, the mixture was partitioned between methylene chloride and saturated sodium carbonate solution, the organic phase was dried over magnesium sulphate and finally the solvent was removed under reduced pressure. The crude product (440 mg) was purified by chromatography on silica gel with a 6.5:1:0.1 mixture of methylene chloride, MeOH and 25% ammonia as the eluent. There were obtained 180 mg (81% of theory) of (3RS,4RS)-4-(3-bromophenyl)-piperidin-3-ol as a light yellow oil. MS: 255, 257 (M)+.

Workup

  1. customSubsequently, the mixture was partitioned between methylene chloride and saturated sodium carbonate solution
  2. dry with materialthe organic phase was dried over magnesium sulphate
  3. customfinally the solvent was removed under reduced pressure
  4. customThe crude product (440 mg) was purified by chromatography on silica gel with a 6.5:1:0.1 mixture of methylene chloride, MeOH and 25% ammonia as the eluent

Sources & evidence

ORD record
ord-6ed8f3332c2049acb16393725b031121
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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