Sodium borohydride → [(2R,3R,4R)-2-[(1R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy]-3-(3,4-difluorophenyl)-tetrahydropyran-4-yl]methanol

HRID 747002ノート

反応式

HRID 747002 の反応式
[BH4-].[Na+].[F:3][C:4]([F:35])([F:34])[C:5]1[CH:6]=[C:7]([C@H:15]([O:17][C@@H:18]2[C@@H:23]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=3)[C@H:22]([CH:32]=[O:33])[CH2:21][CH2:20][O:19]2)[CH3:16])[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1>CO>[F:35][C:4]([F:3])([F:34])[C:5]1[CH:6]=[C:7]([C@H:15]([O:17][C@@H:18]2[C@@H:23]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=3)[C@H:22]([CH2:32][OH:33])[CH2:21][CH2:20][O:19]2)[CH3:16])[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 86601747(2R,3R,4R)-2-[(1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-3-(3,4-difluorophenyl)-tetrahydropyran-4-carbaldehyde

生成物 1

HCID 11420320[(2R,3R,4R)-2-[(1R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy]-3-(3,4-difluorophenyl)-tetrahydropyran-4-yl]methanol収率 93.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium borohydride (24 mg, 0.63 mmol) was added to solution of 2-[1-{(2R,3R,4R)-2-[(1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-3-(3,4-difluorophenyl)-tetrahydropyran-4-carbaldehyde (see Example 2 in WO 02/16344; 107 mg, 0.23 mmol) in methanol (3 ml). The mixture was stirred for 30 minutes then quenched with saturated aqueous NaHCO3 and extracted into ethyl acetate. The combined organic extracts were dried and concentrated to give the title compound (104 mg).

後処理

  1. customthen quenched with saturated aqueous NaHCO3
  2. extractionextracted into ethyl acetate
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-7a72c20896614903831681d05465cae7
出典データセット
uspto-grants-2008_07
特許番号
US07393858B2

反応ノート

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