4-Methylmorpholine → HCID 66662215, compound

HRID 969116Notes

Reaction equation

HRID 969116 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

4

Reactant 3

HCID 79724-MethylmorpholineHCID 2724699PyBOPHCID 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

  1. customThe crude product was purified by prep-LCMS

Sources & evidence

ORD record
ord-49c4d4146f0b452d96262e8b1072f2fe
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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