Water → HCID 178444568, compound

HRID 525475Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][C@H:24]4[CH2:29][CH2:28][C@@H:27]([C:30]([CH3:34])([CH3:33])[CH2:31][CH3:32])[CH2:26][CH2:25]4)[CH:19]=3)[CH:14]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Li+].O1CCCC1.O>>[C:30]([C@@H:27]1[CH2:28][CH2:29][C@H:24]([O:23][C:18]2[CH:19]=[C:20]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([CH2:12][N:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)[CH:22]=[CH:21]3)[CH2:25][CH2:26]1)([CH2:31][CH3:32])([CH3:33])[CH3:34]

Participants

Reactant 4

HCID 962Water

HCID 3939Lithium Hydroxide

HCID 8028Tetrahydrofuran

HCID 178469208HCID 178469208, compound

Product 1

HCID 178444568HCID 178444568, compound

Procedure

A solution of 1-{6-[cis-4-(1,1-dimethyl-propyl)-cyclohexyloxy]-naphthalen-2-ylmethyl}-piperidine-4-carboxylic acid ethyl ester (0.382 g, 0.820 mmol) and lithium hydroxide (196 mg, 8.20 mmol) in tetrahydrofuran (3.32 mL, 41.0 mmol) and water (0.738 mL, 41.0 mmol) was stirred at room temperature overnight. LCMS showed a single desired product peak Rt=1.78 min, m/z=438.40 [M+1], 100%. The solvent was concentrated and neutralized with concentrated HCl. The solid was suspended with water and filtered and washed thoroughly with water and ether then dried to give a white solid (86.9 mg, 24%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.81-0.90 (m, 9H), 1.19-1.70 (m, 10H), 2.19 (d, J=13.99 Hz, 2H), 2.67 (s, 2H), 4.45 (s, 2H), 4.78 (t, J=2.45 Hz, 1H), 7.26 (dd, J=8.91, 2.45 Hz, 1H), 7.31 (d, J=2.26 Hz, 1H), 7.53 (dd, J=8.50, 1.73 Hz, 1H), 7.86 (dd, J=8.69, 3.42 Hz, 2H), 7.96 (s, 1H).

Sources & evidence

ORD record: ord-ef9787980c734324bec7ed16aa0cd91e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340527B2

Reaction notes

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