Formic Acid → (9aS)-8-azetidin-3-ylhexahydropyrazino[2,1-c][1,4]oxazin-4(3H)-one

HRID 2063319Notes

Reaction equation

C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:21][CH2:20][N:19]4[C@H:14]([CH2:15][O:16][CH2:17][C:18]4=[O:22])[CH2:13]3)[CH2:9]2)C=CC=CC=1.C(O)=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH:8]1[CH2:11][CH:10]([N:12]2[CH2:21][CH2:20][N:19]3[C@H:14]([CH2:15][O:16][CH2:17][C:18]3=[O:22])[CH2:13]2)[CH2:9]1

Participants

Conditions

Temperature: 120 °C

Procedure

(9aS)-8-[1-(Diphenylmethyl)azetidin-3-yl]hexahydropyrazino-[2,1-c][1,4]oxazin-4(3H)-one (85 mg, 0.22 mmol) was dissolved in ethanol (18 mL). The solution was transferred to a 25 mL vial, which contained ethanol (2 mL), 10% palladium on carbon (0.1 g), formic acid (0.1 g, 2.2 mmol) and ammonium formate (0.2 g, 3.17 mmol). The mixture was heated for 5 min at 120° C. using microwave single node heating. The catalyst was filtered off and the solution of crude (9aS)-8-azetidin-3-ylhexahydropyrazino[2,1-c][1,4]oxazin-4(3H)-one was used in the next step without purification and quantification.

Workup

temperatureheating
filtrationThe catalyst was filtered off
customthe solution of crude (9aS)-8-azetidin-3-ylhexahydropyrazino[2,1-c][1,4]oxazin-4(3H)-one was used in the next step without purification and quantification

Sources & evidence

ORD record: ord-02720b6636034bc5a193337f120f8bf1
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288370B2

Reaction notes

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