Borane → HCID 69428429, compound

HRID 458378Notes

Reaction equation

HRID 458378 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11](O)=[O:12])[CH2:7][N:6]1[S:14]([CH3:17])(=[O:16])=[O:15])=[O:4].B>O1CCCC1>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][N:6]1[S:14]([CH3:17])(=[O:15])=[O:16])=[O:4]

Participants

4

Reactant 2

HCID 6331BoraneHCID 69433575(2RS,5RS)-1-methanesulfonyl-piperidine-2,5-dicarboxylic acid 2-methyl ester

Product 1

HCID 69428429HCID 69428429, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (2RS,5RS)-1-methanesulfonyl-piperidine-2,5-dicarboxylic acid 2-methyl ester (10.7 g) in tetrahydrofuran was added a 1 M borane solution in tetrahydrofuran (215 ml) within 0.5 h at 0° C. The reaction mixture was stirred for 4 h at 0° C., poured onto ice/saturated sodium bicarbonate solution and concentrated. The aqueous residue was extracted with EtOAc. The organic phase was washed with brine, dried over magnesium sulphate and concentrated. The residue was chromatographed on silica gel using EtOAc/hexane 1:1 and 3:2 as eluents to obtain (2RS,5RS)-5-hydroxymethyl-1-methanesulfonyl-piperidine-2-carboxylic acid methyl ester (8.1 g) as a colourless solid, MS: 206 (100%, M+-59).

Workup

  1. additionpoured onto ice/saturated sodium bicarbonate solution
  2. concentrationconcentrated
  3. extractionThe aqueous residue was extracted with EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-a16e22f2424a4b3ebfa0a1474ceffa2a
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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