Hydrogen chloride-ethyl acetate → (6r)-6-(Methoxymethyl)-3-[2-(methoxymethyl)pyrrolidin-1-yl]-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine hydrochloride

HRID 1877900Notes

Reaction equation

C([N:8]1[CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH:20]3[CH2:24][O:25][CH3:26])=[N:18][C:12]=2[O:11][C@@H:10]([CH2:27][O:28][CH3:29])[CH2:9]1)C1C=CC=CC=1.C(OCC)(=O)C.[ClH:36]>CO.[OH-].[OH-].[Pd+2]>[ClH:36].[CH3:29][O:28][CH2:27][C@H:10]1[CH2:9][NH:8][CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH:20]3[CH2:24][O:25][CH3:26])=[N:18][C:12]=2[O:11]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (6R)-8-benzyl-6-(methoxymethyl)-3-[2-(methoxymethyl)pyrrolidin-1-yl]-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine (329 mg) in methanol (10 mL) was added 20% Pd(OH)2/C (40 mg), and the mixture was stirred under a hydrogen atmosphere at 50° C. for 3 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. To a solution of the obtained crude product in ethyl acetate (10 mL) was added a 4 N hydrogen chloride-ethyl acetate solution (227 μL), and the mixture was stirred for 30 min. The reaction mixture was filtered, and the obtained crystals were washed with ethyl acetate to give the title compound (155 mg, 54%).

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customTo a solution of the obtained crude product in ethyl acetate (10 mL)
stirringthe mixture was stirred for 30 min
filtrationThe reaction mixture was filtered
washthe obtained crystals were washed with ethyl acetate

Sources & evidence

ORD record: ord-80e8ef11036e4130b01b5d727c103832
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314088B2

Reaction notes

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