4-Hydroxypyrrolidine → HCID 68153549, compound

HRID 1405419Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]([N:10]2[CH2:15][CH2:14][C:13]3([N:20]([CH3:21])[CH2:19][CH2:18][N:17]4[C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=[C:16]34)[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:29]1[CH2:33][CH2:32][CH:31]([OH:34])[CH2:30]1>>[OH:34][CH:31]1[CH2:32][CH2:33][N:29]([C:2]2[C:7]([C:8]([N:10]3[CH2:11][CH2:12][C:13]4([N:20]([CH3:21])[CH2:19][CH2:18][N:17]5[C:22]([C:25]([F:27])([F:26])[F:28])=[CH:23][CH:24]=[C:16]45)[CH2:14][CH2:15]3)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:30]1

Participants

Reactant 2

HCID 982104-Hydroxypyrrolidine2×

HCID 86668530HCID 86668530, compound

Product 1

HCID 68153549HCID 68153549, compound

Conditions

Temperature: 80 °C

Procedure

A mixture of (2-Chloro-3-pyridyl)-[2-methyl-6-(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine]-1′-yl]methanone (0.1 mol) and pyrrolidin-3-ol (0.3 mmol) DMF (0.5 mL) was stirred at 80° C. for 16 h. Additional pyrrolidin-3-ol (0.5 mmol) was added and the mixture was stirred at 150° C. for 16 h. The mixture was filtered and was subjected to preparatory-HPLC (10-90% ACN in water) to give (2-(3-hydroxypyrrolidin-1-yl)pyridin-3-yl)(2′-methyl-6′-(trifluoromethyl)-3′,4′-dihydro-2′H-spiro[piperidine-4,1′-pyrrolo[1,2-a]pyrazine]-1-yl)methanone. ESI-MS m/z calc. 463.5, found 464.3 (M+1)+; Retention time: 0.75 minutes (3 min run).

Workup

stirringthe mixture was stirred at 150° C. for 16 h
filtrationThe mixture was filtered

Sources & evidence

ORD record: ord-7de29643d8fe4634a611581ae148a83f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916565B2

Reaction notes

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