Hydrochloric Acid → (r)-2-(5-Bromo-2-difluoromethoxy-benzyl)-morpholine

HRID 2253007Notes

Reaction equation

HRID 2253007 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=2[O:22][CH:23]([F:25])[F:24])[CH2:9]1)(OC(C)(C)C)=O.Cl.C(O)(=O)/C=C/C(O)=O>CC(O)C.C(OCC)C>[Br:21][C:19]1[CH:18]=[CH:17][C:16]([O:22][CH:23]([F:25])[F:24])=[C:15]([CH:20]=1)[CH2:14][C@H:10]1[O:11][CH2:12][CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 444972Fumaric AcidHCID 67073021N-Boc-(R)-2-(5-bromo-2-difluoromethoxy-benzyl)-morpholine

Product 1

HCID 11573334(r)-2-(5-Bromo-2-difluoromethoxy-benzyl)-morpholine

Reagents, catalysts & solvents 1

HCID 22147583Diethyl ether 2-propanolSolvent

Procedure

N-Boc-(R)-2-(5-bromo-2-difluoromethoxy-benzyl)-morpholine, was deprotected using hydrogen chloride (4M, in methanol) and isolated using SCX-2 columns as described for example 4 followed by treatment with fumaric acid in IPA-diethyl ether afforded the morpholine example 61 as the fumarate salt as a white solid (108 mg, 30%).

Workup

  1. customisolated

Sources & evidence

ORD record
ord-b39036d72b7d4d40a24391ae7e872438
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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