Borane;tetrahydrofuran → HCID 51001414, compound

HRID 2381183Notes

Reaction equation

HRID 2381183 reaction equation
[F:1][C:2]([F:32])([F:31])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C@H:13]2[CH2:18][CH2:17][N:16]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C@H:15]([CH2:29][OH:30])[CH2:14]2)=[O:12])=[CH:6][CH:5]=1.[C:33]1([CH3:65])[CH:38]=[CH:37][C:36]([S:39]([N:42]2[CH2:47][CH2:46][C@H:45]([C:48](=[O:61])[NH:49][C:50]3[CH:55]=[CH:54][C:53]([O:56][C:57]([F:60])([F:59])[F:58])=[CH:52][CH:51]=3)[CH2:44][C@H:43]2[C:62]([OH:64])=[O:63])(=[O:41])=[O:40])=[CH:35][CH:34]=1.B.C1COCC1>>[F:32][C:2]([F:1])([F:31])[O:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][N:16]([S:19]([C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)(=[O:21])=[O:20])[C@@H:15]([CH2:29][OH:30])[CH2:14]2)=[O:12])=[CH:8][CH:9]=1.[C:33]1([CH3:65])[CH:34]=[CH:35][C:36]([S:39]([N:42]2[CH2:47][CH2:46][C@@H:45]([C:48](=[O:61])[NH:49][C:50]3[CH:55]=[CH:54][C:53]([O:56][C:57]([F:60])([F:59])[F:58])=[CH:52][CH:51]=3)[CH2:44][C@@H:43]2[C:62]([OH:64])=[O:63])(=[O:41])=[O:40])=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 2723981Borane;tetrahydrofuranHCID 51001413HCID 51001413, compoundHCID 69812375HCID 69812375, compound

Product 2

HCID 51001414HCID 51001414, compoundHCID 69811425HCID 69811425, compound

Procedure

In analogy to example 36 step C) the desired racemic mixture of (2S,4S)-2-hydroxymethyl-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid (4-trifluoromethoxy-phenyl)-amide and (2R,4R)-2-hydroxymethyl-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid (4-trifluoromethoxy-phenyl)-amide (0.09 g) was obtained from the reaction of a racemic mixture of (2S,4S)-1-(toluene-4-sulfonyl)-4-(4-trifluoromethoxy-phenylcarbamoyl)-piperidine-2-carboxylic acid and (2R,4R)-1-(toluene-4-sulfonyl)-4-(4-trifluoromethoxy-phenylcarbamoyl)-piperidine-2-carboxylic acid (0.22 g) and borane-THF complex (1 molar in THF, 0.68 ml) as a white solid. MS (ESI): 473.2 (MH+).

Sources & evidence

ORD record
ord-a7f1620a7aa14de1bbd3203d989f3260
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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