Hydrochloric Acid → 1-(2-(Tert-butoxycarbonylamino)acetyl)-4-(hydroxymethyl)piperidine-4-carboxylic acid

HRID 655969Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([N:12]1[CH2:17][CH2:16][C:15]([CH2:22][OH:23])([C:18]([O:20]C)=[O:19])[CH2:14][CH2:13]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.CO>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([N:12]1[CH2:13][CH2:14][C:15]([CH2:22][OH:23])([C:18]([OH:20])=[O:19])[CH2:16][CH2:17]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 1-(2-(tert-butoxycarbonylamino)acetyl)-4-(hydroxymethyl)piperidine-4-carboxylate (2.5 g, 7.56 mmol, 1.0 equiv.) in THF (10 mL) and CH3OH (10 mL) was added aqueous LiOH (2N, 7.56 mL, 15.13 mmol, 2.0 equiv.). The reaction mixture was stirred at 60° C. for 1 h. The reaction mixture was neutralized with HCl (1 N) and was concentrated to dryness to give 1-(2-(tert-butoxycarbonylamino)acetyl)-4-(hydroxymethyl)piperidine-4-carboxylic acid (3.0 g), which was used without further purification. LRMS (M-Boc+H+) m/z 261.0.

Workup

concentrationwas concentrated to dryness

Sources & evidence

ORD record: ord-f6ee85bcdffe4c29bf4ffe8ab274a6d5
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071625B2

Reaction notes

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