Methanol → tert-Butyl 4-(hydroxymethyl)-4-methoxypiperidine-1-carboxylate

HRID 1840599Notes

Reaction equation

HRID 1840599 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]2([O:13][CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH2:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:28]O>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([O:13][CH3:28])([CH2:12][OH:16])[CH2:14][CH2:15]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

Product 1

HCID 23447302tert-Butyl 4-(hydroxymethyl)-4-methoxypiperidine-1-carboxylate

Procedure

To a solution of 6-(tert-butoxycarbonyl)-1-oxa-6-azaspiro[2,5]octane (17.5 g) in methanol (250 ml) was added p-toluene sulfonic acid hydrate (285 mg), and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and to the residue was added ethyl acetate. The mixture was washed with sodium bicarbonate solution and saturated brine, dried and concentrated, and the residue was crystallized from ice-cooled hexane to give colorless solid of 1-(tert-butoxycarbonyl)-4-methoxy-4-piperidinemethanol (9.32 g).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue was added ethyl acetate
  3. washThe mixture was washed with sodium bicarbonate solution and saturated brine
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was crystallized from ice-
  7. temperaturecooled hexane

Sources & evidence

ORD record
ord-9332446a54b74d31b0c6b49623af784c
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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