methyl 4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzoate → 2-(N-Boc-piperidine-4-yloxy)-4-(tert-butyl)benzoic acid

HRID 1445456Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[CH:21][C:16]=2[C:17]([O:19]C)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[CH:21][C:16]=2[C:17]([OH:19])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

In a 50 ml RBF was suspended methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-tert-butylbenzoate (2.4 g, 6.1 mmol) in 25 ml of 3:1 THF:water to give a light emulsion, then was added solid LiOH monohydrate (567 mg, 13.5 mmol), the flask was fitted with a reflux condenser, and the mixture was heated at 50° C. with stirring for 16 h. The mixture was diluted with 75 ml water and washed twice with diethyl ether. The aqueous layer was acidified to about pH 2 with 1 N NaHSO4, and the resulting slurry extracted twice with 100 ml portions of EtOAc. The combined EtOAc layers were washed with brine, dried, then concentrated in vacuo to afford 2.1 g (91%) of the title acid as a brittle white foam.

Workup

customthe flask was fitted with a reflux condenser
washwashed twice with diethyl ether
extractionthe resulting slurry extracted twice with 100 ml portions of EtOAc
washThe combined EtOAc layers were washed with brine
customdried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ff9417e5950043d8a84ecf34d20bf9c1
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666866B2

Reaction notes

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