Acetate → Uniconazole

HRID 1165372

反応式

HRID 1165372 の反応式
Cl.N[C@@H](CC(C)C)C(C1C=CC=CC=1)(C1C=CC=CC=1)O.C([O-])(=O)C.[BH4-].[Na+].C(O)(=O)C.[Cl:32][C:33]1[CH:38]=[CH:37][C:36](/[CH:39]=[C:40](/[N:47]2[CH:51]=[N:50][CH:49]=[N:48]2)\[C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])=[CH:35][CH:34]=1>>[Cl:32][C:33]1[CH:38]=[CH:37][C:36](/[CH:39]=[C:40](/[N:47]2[CH:51]=[N:50][CH:49]=[N:48]2)\[CH:41]([OH:46])[C:42]([CH3:45])([CH3:44])[CH3:43])=[CH:35][CH:34]=1

参加物

7

反応物 6

HCID 175AcetateHCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10913254(E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-oneHCID 10945486(S)-(-)-2-Amino-4-methyl-1,1-diphenyl-1-pentanol

生成物 1

HCID 6436604Uniconazole収率 73%

実験手順

Reaction was carried out in the same manner as in Example 1 except that the hydrochloride of (S)-2-amino-1,1-diphenyl-4-methylpentan-1-ol was replaced by the acetate thereof, the amount of sodium borohydride used was 0.075 g (1.98 mmoles), and that the reaction was carried out for 91 hours with addition of 0.0162 g (0.27 mmole) of acetic acid to (E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one, to obtain (+)-(E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-ol. The conversion was 100%, and the composition of the product was: E-form alcohol, 90.3%; Z-form alcohol, 6.3%; and saturated alcohol, 3.4%. The enantiomer ratio of the E-form alcohol was: (+)-isomer, 86.5% and (-)-isomer, 13.5%. The optical yield was 73%.

後処理

  1. customReaction

出典と根拠

ORDレコード
ord-f1088bbc03774d578527c4a5e7e3516a
出典データセット
uspto-grants-1990_03
特許番号
US04908455

関連ノート

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