Sodium Methoxide → HCID 58551209, compound

HRID 1908063Notes

Reaction equation

Br[CH2:2][C:3]1[CH:28]=[CH:27][C:6]2[N:7]3[C:24]([C:25]#[N:26])=[CH:23][CH:22]=[C:8]3[C:9]3([CH2:15][CH2:14][N:13](C(=O)C(F)(F)F)[CH2:12][CH2:11]3)[O:10][C:5]=2[CH:4]=1.[CH3:29][O-:30].[Na+]>>[CH3:29][O:30][CH2:2][C:3]1[CH:28]=[CH:27][C:6]2[N:7]3[C:24]([C:25]#[N:26])=[CH:23][CH:22]=[C:8]3[C:9]3([CH2:11][CH2:12][NH:13][CH2:14][CH2:15]3)[O:10][C:5]=2[CH:4]=1

Participants

Reactant 2

HCID 10942334Sodium Methoxide

HCID 58550991HCID 58550991, compound

Product 1

HCID 58551209HCID 58551209, compoundYield 24.9%

Procedure

7′-(Bromomethyl)-1-(2,2,2-trifluoroacetyl)spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]-benzoxazine]-1′-carbonitrile (53.2 mg, 0.117 mmol) was treated with sodium methoxide (36 mg, 0.67 mmol) at room temperature. The mixture was allowed to stir for 5 h at room temperature before it was concentrated under reduced pressure. The residue was taken up in ethyl acetate, filtered, and concentrated to give 7′-(methoxymethyl)spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1′-carbonitrile (9.0 mg, 4%). ESI-MS m/z calc. 309.2. found 310.3 (M+1)+; Retention time 0.97 minutes (3 min run).

Workup

concentrationwas concentrated under reduced pressure
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-df156a9d1e66458ba59137223e31f74e
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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