Sodium triacetoxyborohydride → (3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)-1-(oxetan-3-yl)piperidine

HRID 633418ノート

反応式

HRID 633418 の反応式
[F:1][C@H:2]1[C@H:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[C:18]([F:21])([F:20])[F:19])[CH2:6][CH2:5][NH:4][CH2:3]1.[O:22]1[CH2:25][C:24](=O)[CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:1][C@H:2]1[C@H:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[C:18]([F:21])([F:19])[F:20])[CH2:6][CH2:5][N:4]([CH:24]2[CH2:25][O:22][CH2:23]2)[CH2:3]1

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 86704511(3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine

生成物 1

HCID 86704512(3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)-1-(oxetan-3-yl)piperidine収率 66%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

A solution of (3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine (1.3 g, 1.0 eq, 4.3 mmol) and oxetan-3-one (0.43 g, 1.4 eq, 6.0 mmol) in 1,2-dichloroethane (50 mL) was stirred at room temperature for 30 minutes. Sodium triacetoxyborohydride (1.6 g, 1.8 eq, 7.7 mmol) was added in portions to the above solution and the heterogeneous mixture was stirred at room temperature overnight. Work-up and purification of the crude mixture used the same conditions as Example 88 above for Compound 120, and gave the product in 66% yield.

後処理

  1. custompurification of the crude mixture
  2. customgave the product in 66% yield

出典と根拠

ORDレコード
ord-190aa8d0194843319def9582db91cafb
出典データセット
uspto-grants-2016_04
特許番号
US09321763B2

反応ノート

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