4-Methylmorpholine → HCID 66662215, compound

HRID 557854Notes

Reaction equation

C[C:2]1([CH3:15])[C@H:6]2[CH2:7][CH2:8][C@:3]1([CH2:10]S(O)(=O)=O)[C:4](=[O:9])[CH2:5]2.[NH:16]1[CH2:20][CH2:19][C@@:18]2([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[C:22](=[O:29])[O:21]2)[CH2:17]1.F[P-](F)(F)(F)(F)F.[N:37]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)[C:41]2C=CC=CC=2N=N1.CN1CCOCC1>>[N:37]1[CH:5]=[CH:6][C:2]([C:3]2([C:4]([N:16]3[CH2:20][CH2:19][C@@:18]4([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[C:22](=[O:29])[O:21]4)[CH2:17]3)=[O:9])[CH2:8][CH2:7][CH2:10]2)=[CH:15][CH:41]=1

Participants

Reactant 3

HCID 79724-Methylmorpholine

HCID 2724699PyBOP

HCID 86602280HCID 86602280, compound

Product 1

HCID 66662215HCID 66662215, compound

Procedure

Lithium hydroxide, monohydrate (0.013 g, 0.00031 mol) was added to a solution of ethyl 1-pyridin-4-ylcyclobutanecarboxylate (32 mg, 0.00016 mol) in tetrahydrofuran (1.6 mL, 0.020 mol) and water (0.3 mL, 0.02 mol). The mixture was stirred at room temperature until the reaction was complete. The mixture was acidified (to pH=5) with 4 M HCl (75 μl) and concentrated to afford the carboxylic acid. Then [(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid-(1R)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (1:1) (0.033 g, 0.000078 mol) and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (0.041 g, 0.000078 mol) were added to the above crude product of the carboxylic acid, followed by 4-methylmorpholine (6.0 μL, 0.00055 mol). The reaction mixture was stirred at room temperature for 2 hours. The crude product was purified by prep-LCMS. LC/MS:349.1 (M+H+).

Workup

customThe crude product was purified by prep-LCMS

Sources & evidence

ORD record: ord-589953ef5bd0409095bb3d612924ec33
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058288B2

Reaction notes

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