Acetic Acid → HCID 11822675, compound

HRID 1374418Notes

Reaction equation

HRID 1374418 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5](=[O:15])[CH2:4][N:3]1[C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[OH:15][CH:5]1[CH2:4][N:3]([C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])[C@H:2]([CH3:1])[CH2:7][CH:6]1[C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 10957456HCID 10957456, compound

Product 1

HCID 11822675HCID 11822675, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-allyl 4-tert butyl (2R)-2-methyl-5-oxo-1,4-piperidinedicarboxylate (1.93 g, 6.5 mmol) in methanol (40 ml) were added acetic acid (0.45 ml, 7.9 mmol) and sodium cyanoborohydride (0.49 g, 7.8 mmol), and the mixture was stirred at room temperature for 20 minutes. The solvent was removed in vacuo and the residue was purified by silica gel chromatography to give 1-allyl 4-tert-butyl (2R)-5-hydroxy-2-methyl-1,4-piperidinedicarboxylate (1.85 g, 95%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-caa23d3d2a59413cb0802f063886d52e
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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