Sodium Hydroxide → tert-butyl (3R)-3-(hydroxymethyl)piperidine-1-carboxylate

HRID 1012240Notes

Reaction equation

HRID 1012240 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12][CH2:11][CH2:10][C@@H:9]([C:13](OCC)=[O:14])[CH2:8]1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[OH:14][CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][N:7]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:8]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 15144461-tert-Butyl 3-ethyl (3R)-piperidine-1,3-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1514447tert-butyl (3R)-3-(hydroxymethyl)piperidine-1-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (2.9.0 g, 76.3 mmol) in tetrahydrofuran (100 ml) was added a solution of 1-tert-butyl 3-ethyl (R)-piperidine-1,3-dicarboxylate (16.30 g, 63.6 mmol) in tetrahydrofuran (60 ml) over 20 min under ice-cooling, and the mixture was further stirred for 20 min. To the reaction mixture were successively added water (2.9 ml), 4N aqueous sodium hydroxide solution (2.9 ml), water (8.7 ml) and anhydrous sodium sulfate, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered, and the solvent was evaporated under reduced pressure to give tert-butyl (R)-3-hydroxymethylpiperidine-1-carboxylate (13.00 g, yield 95.0%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1cb7fedc064a4927a69298f62326cc32
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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