Acetic Acid → HCID 86592519, compound

HRID 1374411Notes

Reaction equation

HRID 1374411 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C@H:6]1[CH2:11][CH:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:9](=[O:19])[CH2:8][N:7]1[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[OH:19][CH:9]1[CH2:8][N:7]([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[C@@H:6]([CH2:5][O:4][CH2:3][O:2][CH3:1])[CH2:11][CH:10]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 11121858HCID 11121858, compound

Product 1

HCID 86592519HCID 86592519, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-allyl 4-tert-butyl (2R)-2-[(methoxymethoxy)methyl]-5-oxo-1,4-piperidinedicarboxylate (1.21 g, 3.4 mmol) in methanol (40 ml) was added acetic acid (0.235 ml, 4.1 mmol) and sodium cyanoborohydride (0.255 g, 4.1 mmol) and the mixture were stirred at room temperature for 20 minutes. The solvent was removed in vacuo and it was confirmed whether a starting material run out by TLC. When the starting material remained, methanol (40 ml) was added thereto to dissolve the reaction mixture and then the solvent was again removed. Until the starting material run out, the procedure was repeated. After the starting material run out, the residue was purified by silica gel (30 g) chromatography to give 1-allyl 4-tert-butyl (2R)-5-hydroxy-2-[(methoxymethoxy)methyl]-1,4-piperidinedicarboxylate (1.22 g, quantitatively).

Workup

  1. customThe solvent was removed in vacuo and it
  2. additionmethanol (40 ml) was added
  3. dissolutionto dissolve the reaction mixture
  4. customthe solvent was again removed
  5. customthe residue was purified by silica gel (30 g) chromatography

Sources & evidence

ORD record
ord-e571f8b8a1db44359eff07cd59cfd441
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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