Borane → HCID 69428429, compound

HRID 1006847Notes

Reaction equation

HRID 1006847 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-0259a9700c334973af2db17808ab2a9f
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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