Trifluoroacetic acid → (r)-2-(3-Chloro-4-propyloxy-benzyl)-morpholine

HRID 2253005Notes

Reaction equation

HRID 2253005 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]([Cl:22])[CH:16]=2)[CH2:9]1)(OC(C)(C)C)=O.C(N1CCO[C@H](CC2C=CC=C(C=CC3C=NC=CC=3)C=2)C1)(O[C:26](C)([CH3:28])[CH3:27])=O.ICCC.C(O)(C(F)(F)F)=O>>[Cl:22][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[O:21][CH2:27][CH2:26][CH3:28])[CH2:14][C@H:10]1[O:11][CH2:12][CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 336431-IodopropaneHCID 67073025n-Boc-(r)-2-(3-chloro-4-hydroxybenzyl)morpholineHCID 67073511N-Boc-(R)-2-(3-(2-(3-pyridinyl)vinyl)-benzyl)morpholine

Product 1

HCID 11507301(r)-2-(3-Chloro-4-propyloxy-benzyl)-morpholine

Procedure

Example 58 was prepared using the same procedure as described for example 20, starting from N-BOC-(R)-2-(3-chloro-4-hydroxybenzyl)morpholine, example 7, intermediate (a), and 1-iodopropane. The resulting intermediate was deprotected with TFA as described for example 20 to yield the desired morpholine example 58 as a colorless oil (16 mg) after purification by HPLC.

Workup

  1. customExample 58 was prepared

Sources & evidence

ORD record
ord-256ab95aa9974905b602a6e4aa8ac2ee
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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