Sodium Hydroxide → HCID 86657786, compound

HRID 2168649Notes

Reaction equation

HRID 2168649 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][O:15]C(=O)C)[C@H:10]([O:19][CH2:20][O:21][CH3:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][OH:15])[C@H:10]([O:19][CH2:20][O:21][CH3:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86657785HCID 86657785, compound

Product 1

HCID 86657786HCID 86657786, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (±)-cis-4-acetoxymethyl-3-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester (41.9 mmol, 13.3 g) in THF (100 mL), MeOH (25 mL), and 2 N NaOH (25 mL) was stirred for 3 hours at room temperature. The THF and MeOH were removed under reduced pressure. The crude product was extracted from the water layer with ethyl acetate (3×100 mL). The combined ethyl acetate layers were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified on a 110 g SiO2 cartridge using ethyl acetate/hexanes gradient to give (±)-cis-4-hydroxymethyl-3-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester (10.2 g).

Workup

  1. customThe THF and MeOH were removed under reduced pressure
  2. extractionThe crude product was extracted from the water layer with ethyl acetate (3×100 mL)
  3. washThe combined ethyl acetate layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified on a 110 g SiO2 cartridge

Sources & evidence

ORD record
ord-a7f569b60fea4acd8734b5ef77d69e06
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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