(-)-Epichlorohydrin → (r)-2-(2,2-Difluoro-benzo [1,3]dioxol-4-ylmethyl)-morpholine

HRID 2253011Notes

Reaction equation

HRID 2253011 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=2)[CH2:9]1)=O)(C)(C)C.BrC1C2[O:30][C:29]([F:33])([F:32])[O:28]C=2C=CC=1.C([C@@H]1OC1)Cl.[Cl:39][CH2:40][C@H:41]([OH:54])[CH2:42][C:43]1[C:51]2[O:50][C:49]([F:53])([F:52])[O:48][C:47]=2[CH:46]=[CH:45][CH:44]=1>>[Cl:39][CH2:40][C@H:41]([OH:54])[CH2:42][C:43]1[C:51]2[O:50][C:49]([F:53])([F:52])[O:48][C:47]=2[CH:46]=[CH:45][CH:44]=1.[F:32][C:29]1([F:33])[O:30][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][C@H:10]3[O:11][CH2:12][CH2:13][NH:8][CH2:9]3)[C:16]=2[O:28]1

Participants

6

Reactant 4

HCID 2734062(-)-EpichlorohydrinHCID 27732974-Bromo-2,2-difluoro-1,3-benzodioxoleHCID 67073115(R)-1-chloro-3-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-2-propanolHCID 67073309N-Boc-(R)-2-(3-bromobenzyl)morpholine2×

Product 2

HCID 11658928(r)-2-(2,2-Difluoro-benzo [1,3]dioxol-4-ylmethyl)-morpholineHCID 67073115(R)-1-chloro-3-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-2-propanol

Procedure

(R)-1-chloro-3-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-2-propanol was prepared using the same procedure as described for example 2, intermediate (d), but from 4-bromo-2,2-difluoro-benzo[1,3]dioxole and (R)-epichlorohydrin. Example 66 was prepared as described for example 1, intermediate (d), but using (R)-1-chloro-3-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-2-propanol, to obtain the desired morpholine example 66, as a colorless liquid, (0.214 g, 13.6%).

Workup

  1. customExample 66 was prepared

Sources & evidence

ORD record
ord-5a03bf1473ab460f9c59444c089fb8ba
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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