Sodium hydride → tert-Butyl 4-((2-methoxy-5-(2-methyl-2H-tetrazol-5-yl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

HRID 391398Notes

Reaction equation

Br[CH2:2][C:3]1[CH:4]=[C:5]([C:11]2[N:12]=[N:13][N:14]([CH3:16])[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH:17][CH2:18][C:19]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.[H-].[Na+]>CN(C)C=O>[CH3:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([C:11]2[N:12]=[N:13][N:14]([CH3:16])[N:15]=2)=[CH:4][C:3]=1[CH2:2][O:17][CH2:18][C:19]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 0 °C

Procedure

5-(3-(Bromomethyl)-4-methoxyphenyl)-2-methyl-2H-tetrazole (35.0 mg, 0.12 mmol) and tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate (40.0 mg, 0.14 mmol) were combined in dimethylformamide (1 mL) and cooled to 0° C. The reaction was treated with sodium hydride (3.2 mg, 0.14 mmol), stirred at 0° C. for 1 h, and at room temperature overnight. The solvents were removed in vacuo and the crude product purified by column chromatography on silica gel (30% ethyl acetate/hexanes) to afford 30 mg (50%). LC/MS (HPLC method 3): tR=3.29 min, 494.25 (MH)+.

Workup

customat room temperature
customovernight
customThe solvents were removed in vacuo
customthe crude product purified by column chromatography on silica gel (30% ethyl acetate/hexanes)
customto afford 30 mg (50%)

Sources & evidence

ORD record: ord-14031fe91f9f47ad83ebd31b64bb981b
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383821B2

Reaction notes

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