Cyclobutanone → HCID 86600245, compound

HRID 2386972Notes

Reaction equation

HRID 2386972 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[OH:11].[C:12]([N:19]1[CH2:24][CH2:23][CH:22](O)[CH2:21][CH2:20]1)(OC(C)(C)C)=O.[C:26]1(=O)[CH2:29]C[CH2:27]1.O.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([OH:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1>>[S:38]([C:35]1[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=1)([OH:41])(=[O:40])=[O:39].[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:11][CH:22]1[CH2:21][CH2:20][N:19]([CH:12]2[CH2:29][CH2:26][CH2:27]2)[CH2:24][CH2:23]1)[NH2:8]

Participants

5

Reactant 4

HCID 14496CyclobutanoneHCID 221092-Bromo-4-nitrophenol2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 86600245HCID 86600245, compound

Procedure

3-bromo-4-[(1-cyclobutylpiperidin-4-yl)oxy]aniline was obtained according to the method of Example 94, using 2-bromo-4-nitrophenol, N-Boc-4-piperidinol and cyclobutanone as starting materials. By treating this with 1 Eq of p-toluenesulfonic acid monohydrate, the target compound was obtained as a colorless solid. 2-bromo-4-nitrophenol was manufactured by the method described in the literature (J. Org. Chem., Vol. 62, 1997, p. 4504).

Workup

  1. customthe target compound was obtained as a colorless solid

Sources & evidence

ORD record
ord-00c8959156f14d9e8f8d56af056367ce
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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