Trifluoroacetic acid → (r)-2-(3-Bromo-4-butoxy-benzyl)-morpholine

HRID 2253008Notes

Reaction equation

HRID 2253008 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([Br:22])[CH:16]=2)[CH2:9]1)(OC(C)(C)C)=O.C(N1CCO[C@H:32]([CH2:36][C:37]2C=CC=C(C=CC3C=NC=CC=3)C=2)[CH2:31]1)(OC(C)(C)C)=O.BrCCCC.C(O)(C(F)(F)F)=O>>[Br:22][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[O:21][CH2:31][CH2:32][CH2:36][CH3:37])[CH2:14][C@H:10]1[O:11][CH2:12][CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8002Butyl bromideHCID 67073493N-BOC-(R)-2-(3-bromo-4-hydroxybenzyl)morpholineHCID 67073511N-Boc-(R)-2-(3-(2-(3-pyridinyl)vinyl)-benzyl)morpholine

Product 1

HCID 11493607(r)-2-(3-Bromo-4-butoxy-benzyl)-morpholine

Procedure

Example 61 was prepared using the same procedure as described for example 4, starting from N-BOC-(R)-2-(3-bromo-4-hydroxybenzyl)morpholine, example 4, intermediate (a), and 1-bromobutane. The resulting intermediate was deprotected with TFA as described for example 4 to yield the desired morpholine example 61 as a colorless oil (28 mg, 63% over 2 steps) after purification by HPLC.

Workup

  1. customExample 61 was prepared

Sources & evidence

ORD record
ord-0703e5b21ead4f74b1dcb85fd4fe70b8
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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