tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate → HCID 86727071, compound

HRID 2175849Notes

Reaction equation

[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH3:11])[C:5]([CH:12]2[CH2:14][O:13]2)=[CH:4][CH:3]=1.[C:15]([N:22]1[CH2:27][CH2:26][NH:25][C@H:24]([CH2:28][OH:29])[CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>C(O)C>[C:8]([C:7]1[C:6]([O:10][CH3:11])=[C:5]([CH:12]([OH:13])[CH2:14][N:25]2[CH2:26][CH2:27][N:22]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:23][C@H:24]2[CH2:28][OH:29])[CH:4]=[CH:3][C:2]=1[F:1])#[N:9]

Participants

Conditions

Temperature: 150 °C

Procedure

6-Fluoro-2-methoxy-3-(oxiran-2-yl)benzonitrile (1.4 g, 7.3 mmol) and (S)-4-N-BOC-2-hydroxymethylpiperazine (3.13 g, 14.5 mmol) were suspended in ethanol (15 mL) then heated in a microwave apparatus for 60 min at 150° C. The reaction mixture was cooled and evaporated to dryness. The residue was purified by chromatography through a 40 g Redi-sep column and eluting with 5% MeOH/95% EtOAc to yield the title compound: LC-MS: M+1=410;

Workup

temperatureThe reaction mixture was cooled
customevaporated to dryness
customThe residue was purified by chromatography through a 40 g Redi-sep column
washeluting with 5% MeOH/95% EtOAc

Sources & evidence

ORD record: ord-40886b71152f4f05b7e9f83abebaf6d1
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062070B2

Reaction notes

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