Piperidine → HCID 57323224, compound

HRID 62565Notes

Reaction equation

N1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C[CH2:10][CH2:9][CH2:8]1.[C:12]([C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[CH:19]=O)([CH3:15])([CH3:14])[CH3:13]>>[C:12]([C:16]1[C:23](=[O:24])[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][C:18](=[CH:19][C:2]#[C:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:6][CH:5]=2)[CH:17]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

Reactant 3

HCID 8082Piperidine

HCID 31268Pyrrolidine

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 57323224HCID 57323224, compound

Procedure

In lieu of piperidine, pyrrolidine was used with 3,5-di-tert-butyl-4-hydroxybenzaldehyde to synthesize the subsequent intermediate 7-pyrrolidinyl quinone methide following the procedure in Example 1 (d). The remainder of the one-pot procedure towards 7-Phace-QM is as detailed in Example 1 (d).

Sources & evidence

ORD record: ord-320674cebadf4dd48475c71140601242
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447002B2

Reaction notes

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