1,2-Dichloroethane → HCID 66970642、化合物

HRID 1361518

反応式

HRID 1361518 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([C:8]2([O:14][CH3:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.[BH-](O[C:28]([CH3:30])=O)(OC(C)=O)OC(C)=O.[Na+].Cl[CH2:33][CH2:34]Cl>>[C@H:34]12[CH2:33][C@H:7]([CH:2]=[CH:3]1)[CH2:6][C@@H:28]2[CH2:30][N:11]1[CH2:10][CH2:9][C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:16][CH3:17])([O:14][CH3:15])[CH2:13][CH2:12]1

参加物

4

反応物 3

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 587722974-(5-Chloro-2-methoxyphenyl)-4-methoxypiperidine

生成物 1

HCID 66970642HCID 66970642、化合物

実験手順

4-(5-Chloro-2-methoxyphenyl)-4-methoxypiperidine 5d (51 mg, 0.2 mmol) was dissolved in 1,2-dichloroethane (1.5 mL) and treated with (S,S,S)-norbornene carboxaldehyde (24 mg, 0.2 mmol, 1.0 eq), followed by the addition of NaBH(OAc)3 (65 mg, 0.3 mmol, 1.5 eq). The reaction was allowed to stir at room temperature for 1 h, quenched with methanol (1 mL) and allowed to stir for another 30 min (until gas evolution stopped). The crude reaction mixture was purified by HPLC (10-99 CH3CN gradient, 0.05% TFA) to provide the desired product 1-(((1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl)methyl)-4-(5-chloro-2-methoxyphenyl)-4-methoxypiperidine (compound no. 140) as the TFA salt. LC/MS (RP-C18, 10-99% CH3CN/0.05% TFA gradient over 5 min) m/z 362.2 [M+H]+, retention time 2.53 min.

後処理

  1. customquenched with methanol (1 mL)
  2. stirringto stir for another 30 min (until gas evolution stopped)
  3. customThe crude reaction mixture
  4. customwas purified by HPLC (10-99 CH3CN gradient, 0.05% TFA)

出典と根拠

ORDレコード
ord-1aa2781b4e1941ba860470fe5eea490a
出典データセット
uspto-grants-2011_02
特許番号
US07880007B2

関連ノート

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