Sodium borohydride → (2S,5S)-1-tert-butyl 2-ethyl 5-hydroxypiperidine-1,2-dicarboxylate

HRID 1406845Notes

Reaction equation

HRID 1406845 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:6][CH2:5]1>CCO>[OH:3][C@@H:4]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[C@H:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70701166(S)-1-tert-butyl 2-ethyl 5-oxopiperidine-1,2-dicarboxylate

Product 1

HCID 86700663(2S,5S)-1-tert-butyl 2-ethyl 5-hydroxypiperidine-1,2-dicarboxylateYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (36 g, 1.0 mol) was added in portions to a solution of (S)-1-tert-butyl 2-ethyl 5-oxopiperidine-1,2-dicarboxylate (250 g, 0.92 mol) in EtOH (1500 mL) at −40° C. The reaction mixture was then stiffed at −40° C. for 0.5 hr then quenched with 10% HOAc solution. After diluting with water, the mixture was extracted with DCM three times. The combined organic layer was concentrated in vacuum and purified by silica gel column chromatography (1:1 petroleum ether/EtOAc) to afford (2S,5S)-1-tert-butyl 2-ethyl 5-hydroxypiperidine-1,2-dicarboxylate (205 g, 80%) as a yellow oil.

Workup

  1. customthen quenched with 10% HOAc solution
  2. additionAfter diluting with water
  3. extractionthe mixture was extracted with DCM three times
  4. concentrationThe combined organic layer was concentrated in vacuum
  5. custompurified by silica gel column chromatography (1:1 petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-e343bdaf23d742e3afede27aeed9955f
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

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