Sodium cyanoborohydride → HCID 58179661, compound

HRID 254000Notes

Reaction equation

HRID 254000 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-54ecc094f35e4168bc7ebd4911f80850
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

Loading…