Phenyl methoxycarbamate → HCID 86629524, compound

HRID 1711160Notes

Reaction equation

[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][C@H:10]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:14][CH2:13]1)[CH3:11])([CH3:4])([CH3:3])[CH3:2].C1([O:33][C:34](=O)[NH:35][O:36][CH3:37])C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][C@H:10]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]([CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:34]([NH:35][O:36][CH3:37])=[O:33])[CH2:14][CH2:13]1)[CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of {(R)-3-[4-(cyclohexylmethyl-amino)-piperidin-1-yl]-butyl}-carbamic acid tert-butyl ester (174 mg, 0.47 mmol) in THF (5 ml) was added methoxy-carbamic acid phenyl ester (94.7 mg, 0.56 mmol). The mixture was stirred at 60° C. for 3 d then concentrated in vacuo. The crude product was purified by flash chromatography (CH2Cl2, 7% MeOH, 1% NH4OH) to afford {(R)-3-[4-(1-cyclohexylmethyl-3-methoxy-ureido)-piperidin-1-yl]-butyl}-carbamic acid tert-butyl ester (105 mg, 50%) as a yellow oil.

Workup

concentrationthen concentrated in vacuo
customThe crude product was purified by flash chromatography (CH2Cl2, 7% MeOH, 1% NH4OH)

Sources & evidence

ORD record: ord-e9b74cc0a1ea49eba042b5cd92d0ab93
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790747B2

Reaction notes

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