Formaldehyde → 2-Methyl-2-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-propionic acid

HRID 538632Notes

Reaction equation

[CH3:1][C:2]([NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)([CH3:6])[C:3]([OH:5])=[O:4].[CH2:15]=O.[H][H]>CCO.[OH-].[OH-].[Pd+2]>[CH3:6][C:2]([N:7]([CH3:15])[CH2:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

1.00 g (4.97 mmol) of 2-methyl-2-[(tetrahydro-pyran-4-ylmethyl)-amino]propionic acid is suspended in 20 mL of EtOH. 350 mg Pd(OH)2 (0.50 mmol, w=20%) are added, followed by 0.74 mL of formaldehyde (9.88 mmol; 37% in water). The suspension is stirred for 24 h at 100° C. and 2916 kPa hydrogen pressure. The reaction mixture is filtered through celite and washed with EtOH. The solvent is removed under reduced pressure to afford 0.90 g of 2-methyl-2-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-propionic acid. Yield: 84%; ESI-MS: 216 [M+H]+

Workup

filtrationThe reaction mixture is filtered through celite
washwashed with EtOH
customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-46646acee75b4dbe817b95c20289b83c
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865744B1

Reaction notes

Loading…