(3S,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-3-methylmorpholin-2-ol → Dibenzyl-{(1S,2S)-2-benzyloxy-1-(3,5-difluorobenzyl)-2-[(3R,5S,6R)-6-(2,2-di-(fluoromethyl)propoxy)-5-methylmorpholin-3-yl]-ethyl}-amine

HRID 20455Notes

Reaction equation

HRID 20455 reaction equation
[F:1][CH2:2][C:3]([CH2:7][F:8])([CH3:6])[CH2:4][OH:5].[CH2:9]([O:16][C@@H:17]([C@@H:43]1[NH:48][C@@H:47]([CH3:49])[CH:46](O)[O:45][CH2:44]1)[C@@H:18]([N:28]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:36]([N:28]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C@@H:18]([CH2:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=1)[C@@H:17]([O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C@H:43]1[CH2:44][O:45][C@@H:46]([O:5][CH2:4][C:3]([CH2:7][F:8])([CH2:2][F:1])[CH3:6])[C@H:47]([CH3:49])[NH:48]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 68561049(3S,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-3-methylmorpholin-2-olHCID 859252012,2-Di-(fluoromethyl)propanol

Product 1

HCID 68563071Dibenzyl-{(1S,2S)-2-benzyloxy-1-(3,5-difluorobenzyl)-2-[(3R,5S,6R)-6-(2,2-di-(fluoromethyl)propoxy)-5-methylmorpholin-3-yl]-ethyl}-amineYield 42.1%

Procedure

React 2,2-di-(fluoromethyl)propanol (2.172 g, 17.5 mmol) with (3S,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-3-methylmorpholin-2-ol (2.004 g, 3.5 mmol) essentially as described in Preparation 307 to provide 1.0 g of the desired compound.

Workup

  1. customas described in Preparation 307

Sources & evidence

ORD record
ord-19fd02864bc24a6d8bad2df46b92293b
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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