Sodium cyanoborohydride → HCID 58179661, compound

HRID 1518553Notes

Reaction equation

HRID 1518553 reaction equation
O[C:2]1([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[BH3-]C#N.[Na+]>ClCCCl.[Zn+2].[I-].[I-]>[S:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 58179496HCID 58179496, compound

Product 1

HCID 58179661HCID 58179661, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of tert-butyl 4-hydroxy-4-(thiophen-2-yl)piperidine-1-carboxylate (6.0 g, 21.2 mmol) in 1,2-dichloroethane at 0° C. was added ZnI2 (10.15 g, 31.8 mmol) in portions. The reaction mixture was stirred for 30 minutes, followed by the addition of NaCNBH3 (2.0 g, 31.8 mmol) in portions. The reaction mixture was slowly warmed to RT and stirred for 2 hours. The reaction was quenched with ice, extracted with CH2Cl2 (2×50 mL), washed with brine solution, dried (Na2SO4), filtered, and concentrated to obtain tert-butyl 4-(thiophen-2-yl)piperidine-1-carboxylate, which was used as is for subsequent reactions without further purification.

Workup

  1. stirringstirred for 2 hours
  2. customThe reaction was quenched with ice
  3. extractionextracted with CH2Cl2 (2×50 mL)
  4. washwashed with brine solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-36f3ac02f666442692641a3d3451ff9c
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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